Microbiocidal n-phenyl-n-{4-(4-pyridyl)-2-pyrimidin-2-yl}-amine derivatives

ABSTRACT

Fungicidal compounds of Formula (I) wherein m is 0, 1, 2 or 3; n and p are independently of each other 0 or 1; R 1  is halogen, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted alkenyloxy, optionally substituted alkynyloxy, optionally substituted thioalkyl optionally substituted aryl, COOR 11 , CONR 12 R 13 , S(O) q R 14 , SO 2 NR 15 R 16  or NR 15a R 16a ; q is 1 or 2; and R 2 , R 2a , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 15a , R 16a , are specified organic groups or a salt thereof; their preparation and compositions containing them.

The present invention relates to novel N-phenyl-[4-(4-pyridyl)-pyrimidin-2-yl]-amine derivatives, to a method of protecting plants against attack or infestation by phytopathogenic organisms, such as nematodes or insects or especially microorganisms, preferably fungi, bacteria and viruses, or combinations of two or more of these organisms, by applying a N-phenyl-[4-(4-pyridyl)-pyrimidin-2-yl]-amine derivative as specified hereinafter to a part and/or to the site of a plant, to the use of said derivative for protecting plants against said organisms, and to compositions comprising said derivative as the active component. The invention further relates to the preparation of these novel N-phenyl-[4-(4-pyridyl)-pyrimidin-2-yl]-amine derivatives.

Certain N-phenyl-4-(4-pyridyl)-2-pyrimidineamine derivatives have been described in the art as having pharmacological properties e.g. in the PCT patent applications WO 95/09851 and WO 95/09853, as tumor-inhibiting anti-cancer substances and in WO 97/19065 and WO98/18782 for the treatment of immune diseases.

Surprisingly, it has now been found that the new N-phenyl-[4-(4-pyridyl)-pyrimidin-2-yl]-amines are effective in plant protection and related areas, showing advantageous properties in the treatment of plant diseases caused by organisms.

The novel N-phenyl-[4-(4-pyridyl)-pyrimidin-2-yl]-amine derivatives according to the invention are those of the formula I

wherein

-   m is 0, 1, 2 or 3; -   n and p are independently of each other 0 or 1; -   R₁ is halogen, optionally substituted alkyl, optionally substituted     alkoxy, optionally substituted alkenyloxy, optionally substituted     alkynyloxy, optionally substituted thioalkyl optionally substituted     aryl, COOR₁₁, CONR₁₂R₁₃, S(O)_(q)R₁₄, SO₂NR₁₅R₁₆ or NR_(15a)R_(16a);     when there is more than on R₁ group, they may be the same or     different; -   q is 1 or 2; -   R₂, R_(2a), R₃, R₄, R₅, R₆, R₇, R₈ are each independently hydrogen,     optionally substituted alkyl, COR₁₇, COOR₁₈ or optionally     substituted aryl, and in addition R₂ and R₃ may also independently     be optionally substituted alkoxy, optionally substituted alkenyloxy,     optionally substituted alkynyloxy, or optionally substituted     alkylthio, COOR₁₉, CONR₂OR₂₁, OH or SH; -   R₆ and R₇ may also be independently halogen, optionally substituted     alkoxy, optionally substituted alkenyloxy, optionally substituted     alkynyloxy, optionally substituted alkenylamino, optionally     substituted alkynylamino, optionally substituted alkylthio,     optionally substituted cycloalkyl, optionally substituted     heteroaryl, optionally substituted hetrocyclyl, optionally     substituted cycloalkyloxy, OH, SH, N₃, NR₂₂R₂₃ or N(R₂₄)COR₂₅; or     the ring members CR₃R₄ or CR₂R_(2A) are independently of each other     a carbonyl group (C═O) or a thonyl group (C═S); -   or one or two of the adjacent pairs of groups R₉ and R₄, R₄ and R₅,     R₅ and R₈, or, if p is zero, R_(2A) and R₈ may form a bond, provided     that if there are 2 double bonds in the ring the double bonds are     not adjacent each other; -   or the pair of groups R₇ and R₅ or the pair of groups R₆ and R₇     together with the atom to which they are attached form a C₃-C₇     saturated ring; -   R₉ is hydrogen, optionally substituted alkyl, optionally substituted     alkenyl or optionally substituted alkynyl; -   R₁₀ is hydrogen, C₁-C₄-alkyl, C₃-C₄-alkenyl, C₃-C₄-alkynyl,     —CH₂OR₂₆, CH₂SR₂₇, —C(O)R₂₈, —C(O)OR₂₉, SO₂R₃₀, SOR₃₁ or SR₃₂; -   R₂₆, R₂₇, R₂₉, R₂₉, R₃₀, R₃₁, R₃₂ are independently C₁-C₈-alkyl     C₁-C₈-alkoxyalkyl, C₁-C₈ haloalkyl or phenylC₁-C₂-alkyl wherein the     phenyl may be substituted by up to three groups selected from halo     or C₁-C₄-alkyl, -   R₁₁, R₁₂, R₁₃, R₁₄, R₁₅, R₁₆R_(15a), R_(16a), R₁₇, R₁₈, R₁₉, R₂₀,     R₂₁, R₂₂, R₂₃, R₂₄, and R₂₅ are independently H or optionally     substituted alkyl; or a salt thereof.

One group of preferred compounds are of those of formula (I′) which are compounds of formula I wherein

-   m is 0, 1, 2 or 3; -   n and p are independently of each other 0 or 1; -   R₁ is halogen, optionally substituted alkyl, optionally substituted     alkoxy, optionally substituted thioalkyl optionally substituted     aryl, COOR₁₁, CONR₁₂R₁₃, S(O)_(q)R₁₄, SO₂NR₁₅R₁₆ or NR_(15a)R_(16a);     when there is more than on R₁ group, they may be the same or     different; -   q is 1 or 2; -   R₂, R_(2a), R₃, R₄, R₅, R₆, R₇, R₈ are each independently hydrogen,     optionally substituted alkyl, COR₁₇, COOR₁₈ or optionally     substituted aryl, and in addition R₂ and R₃ may also independently     be optionally substituted alkoxy or optionally substituted     alkylthio, COOR₁₉, CONR₂₀R₂₁, OH or SH; -   R₆ and R₇ may also be independently halogen, optionally substituted     alkoxy, optionally substituted alkylthio, OH, SH, N₃, NR₂₂R₂₃ or     N(R₂₄)COR₂₅; or the ring members CR₃R₄ or CR₂R_(2A) are     independently of each other a carbonyl group (C═O) or a thiocarbonyl     group (C═S); -   or one or two of the adjacent pairs of groups R₉ and R₄, R₄ and R₈,     R₅ and R₈, or, if p is zero, R_(2A) and R₈ may form a bond, provided     that if there are 2 double bonds in the ring the double bonds are     not adjacent each other; or the pair of groups R₇ and R₈ together     with the atom to which they are attached form a C₃-C₇ saturated     ring; -   R₉ is hydrogen or optionally substituted alkyl; -   R₁₀ is hydrogen, C₁-C₄-alkyl, C₃-C₄-alkenyl, C₃-C₄-alkynyl,     —CH₂OR₂₆, CH₂SR₂₇, —C(O)R₂₈, —C(O)OR₂₉, SO₂R₃₀, SOR₃₁ or SR₃₂; R₂₆,     R₂₇, R₂₉, R₂₉, R₃₀, R₃₁, R₃₂ are independently C₁-C₈-alkyl     C₁-C₈-alkoxyalkyl, C₁-C₈ haloalkyl or phenylC₁-C₂-alkyl wherein the     phenyl may be substituted by up to three groups selected from halo     or C₁-C₄-alkyl, R₁₁, R₁₂, R₁₃, R₁₄, R₁₅, R₁₆R_(15a), R_(16a), R₁₇,     R₁₈, R₁₉, R₂₀, R₂₁, R₂₂, R₂₃, R₂₄, and R₂₅ are independently H or     optionally substituted alkyl; or a salt thereof.

In the context of the present specification alkyl as a group per se and as a structural element of hydroxyalkyl, thioalkyl, alkoxy, alkenyl, alkenyloxy, alkynyl alkynyloxy or haloalkoxy—is preferably C₁-C₆-alkyl, more preferably lower alkyl, and is linear i.e. methyl, ethyl, propyl, butyl, pentyl or hexyl, or branched, e.g. isopropyl, isobutyl, sec.-butyl, tert.-butyl, isopentyl, neopentyl or isohexyl. Lower alkyl is preferably methyl or ethyl.

Specific examples of alkenyl and alkynyl include allyl, 2-butenyl, 3-butenyl, propargyl, 2-butinyl and 3 butynyl.

When present, the optional substituents on an alkyl, alkenyl or alkynyl moiety include one or more of halogen, nitro, cyano, oxo (and acetals and ketals formed therefrom), C₃₋₇ cycloalkyl (itself optionally substituted with C₁₋₆ alkyl or halogen), C₅₋₇ cycloalkenyl (itself optionally substituted with C₁₋₆ alkyl or halogen), hydroxy, C₃₋₁₀ alkoxy, C₃₋₁₀ alkoxy(C₃₋₁₀)alkoxy, C₁₋₆ alkoxy-carbonyl(C₃₋₁₀)alkoxy, C₃₋₁₀haloalkoxy, phenyl(C₁₋₄)alkoxy (where the phenyl group is optionally substituted by one or more of C₁₋₆ alkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkyl, CN, nitro or halogen), C₃₋₇ cycloalkyloxy (where the cycloalkyl group is optionally substituted with C₁₋₆ alkyl or halogen), C₃₋₁₀ alkenyloxy, C₃₋₁₀ alkynyloxy, SH, C₃₋₁₀ alkylthio, C₃₋₁₀ haloalkylthio, phenyl(C₁₋₄)alkylthio (where the phenyl group is optionally substituted by one or more of C₁₋₆ alkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkyl, CN, nitro or halogen), C₃₋₇ cycloalkylthio (where the cycloalkyl group is optionally substituted with C₁₋₆alkyl or halogen), tri(C₁₋₄)alkylsilyl(C₁₋₆)alkylthio, phenylthio (where the phenyl group is optionally substituted by one or more of C₁₋₆ alkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkyl, CN, nitro or halogen), C₁₋₆ alkylsulfonyl, C₁₋₆ haloalkylsulfonyl, C₁₋₆ alkylsulfinyl, CO₁₋₆haloalkylsulfinyl, phenylsulfonyl (where the phenyl group is optionally substituted by one or more of C₁₋₆ alkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkyl, CN, nitro or halogen), tri(C₁₋₄)alkylsilyl, phenyldi(C₁₋₄)alkylsilyl, (C₁₋₄)alkyldiarylsilyl, triphenylsilyl, C₃₋₁₀ alkylcarbonyl, H₀₂C, C₃₋₁₀ alkoxycarbonyl, aminocarbonyl, C₁₋₆ alkylaminocarbonyl, di(C₁₋₆ alkyl)-aminocarbonyl, N-(C₁₋₃ alkyl)-N-(C₁₋₃ alkoxy)aminocarbonyl, C₁₋₆ alkylcarbonyloxy, phenylcarbonyloxy (where the phenyl group is optionally substituted by one or more of C₁₋₆ alkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkyl, CN, nitro or halogen), di(C₁₋₆)alkylaminocarbonyloxy, phenyl (itself optionally substituted by one or more of C₁₋₆ alkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkyl, CN, nitro or halogen), naphthyl (itself optionally substituted by C₁₋₆ alkyl or halogen), heteroaryl (itself optionally substituted by C₁₋₆ alkyl or halogen), heterocyclyl (itself optionally substituted with C₁₋₆ alkyl or halogen), phenyloxy (where the phenyl group is optionally substituted by substituted by one or more of C₁₋₆ alkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkyl, CN, nitro or halogen), naphthyloxy (where the naphthyl group is optionally substituted by C₁₋₆ alkyl or halogen), heteroaryloxy, (where the heteroaryl group is optionally substituted by C₁₋₆ alkyl or halogen), heterocyclyloxy (where the heterocyclyl group is optionally substituted with C₁₋₆ alkyl or halogen), amino, C₁₋₆ alkylamino, di(C₁₋₆) alkylamino, C₁₋₆ alkylcarbonylamino and N-(C₁₋₆)alkylcarbonyl-N-(C₁₋₆)alkylamino.

Preferred substituents on an alkyl, alkenyl or alkynyl moiety include one or more of halogen, nitro, cyano, C₃₋₇ cycloalkyl (itself optionally substituted with C₁₋₆ alkyl or halogen), C₅₋₇ cycloalkenyl (itself optionally substituted with C₁₋₆ alkyl or halogen), hydroxy, C₃₋₁₀ alkoxy, C₃₋₁₀ alkoxy(C₃₋₁₀)alkoxy, C₁₋₆ Lkoxy-carbonyl(C₃₋₁₀)alkoxy, C₃₋₁₀haloalkoxy, phenyl(C₁₋₄)alkoxy (where the phenyl group is optionally substituted by C₁₋₆ alkyl or halogen), C₃₋₇ cycloalkyloxy (where the cycloalkyl group is optionally substituted with C₁₋₆ alkyl or halogen), C₃₋₁₀alkenyloxy, C₃₋₁₀alkynyloxy, SH, C₃₋₁₀ alkylthio, C₃₋₁₀haloalkylthio, phenyl(C₁₋₄)alkylthio (where the phenyl group is optionally substituted by C₁₋₆ alkyl or halogen), C₃₋₇ cycloalkylthio (where the cycloalkyl group is optionally substituted with C₁₋₆ alkyl or halogen), tri(C₁₋₄)alkylsilyl(C₁₋₆)alkylthio, phenylthio (where the phenyl group is optionally substituted by C₁₋₆ alkyl or halogen), C₁₋₆ alkylsulfonyl, C₁₋₆ haloalkylsulfonyl, C₁₋₆ alkylsulfinyl, C₁₋₆ haloalkylsulfinyl, phenylsulfonyl (where the phenyl group is optionally substituted by C₁₋₆ alkyl or halogen), tri(C₁₋₄)alkylsilyl, phenyldi(C₁₋₄)alkylsilyl, (C₁₋₄)alkyldiarylsilyl, triphenylsilyl, C₃₋₁₀ alkylcarbonyl, HO₂C, C₃₋₁₀ alkoxycarbonyl, aminocarbonyl, C₁₋₆ alkylaminocarbonyl, di(C₁₋₆ alkyl)-aminocarbonyl, N-(C₁₋₃ alkyl)-N-(C₁₋₃ alkoxy)aminocarbonyl, C₁₋₆ alkylcarbonyloxy, phenylcarbonyloxy (where the phenyl group is optionally substituted by C₁₋₆ alkyl or halogen), di(C₁₋₆)alkylaminocarbonyloxy, phenyl (itself optionally substituted by C₁₋₆ alkyl or halogen), heteroaryl (itself optionally substituted by C₁₋₆ alkyl or halogen), heterocyclyl (itself optionally substituted with C₁₋₆ alkyl or halogen), phenyloxy (where the phenyl group is optionally substituted by C₁₋₆ alkyl or halogen), heteroaryloxy, (where the heteroaryl group is optionally substituted by C₁₋₆ alkyl or halogen), heterocyclyloxy (where the heterocyclyl group is optionally substituted with C₁₋₆ alkyl or halogen), amino, C₁₋₆ alkylamino, di(C₁₋₆) alkylamino, C₁₋₆ alkylcarbonylamino and N-(C₁₋₆)alkylcarbonyl-N—(C₁₋₆)alkylamino.

More preferred substituents on an alkyl, alkenyl and alkynyl moiety include one or more of halogen, nitro, cyano, C₃₋₇ cycloalkyl (itself optionally substituted with C₁₋₆ alkyl or halogen), hydroxy, C₃₋₁₀ alkoxy, C₃₋₁₀ alkoxy(C₃₋₁₀)alkoxy, C₁₋₆ alkoxy-carbonyl(C₃₋₁₀)alkoxy, C₃₋₁₀haloalkoxy, SH, C₃₋₁₀alkylthio, C₃₋₁₀ haloalkylthio, C₁₋₆alkylsulfonyl, C₁₋₆ haloalkylsulfonyl, C₁₋₆ alkylsulfinyl, C₁₋₆ haloalkylsulfinyl, phenylsulfonyl (where the phenyl group is optionally substituted by C₁₋₆ alkyl or halogen), HO₂C, C₃₋₁₀ alkoxycarbonyl, aminocarbonyl, C₁₋₆ alkylaminocarbonyl, heteroaryl (itself optionally substituted by C₁₋₆ alkyl or halogen), heterocyclyl (itself optionally substituted with C₁₋₆ alkyl or halogen), phenyloxy (where the phenyl group is optionally substituted by C₁₋₆ alkyl or halogen), amino, C₁₋₆alkylamino and di(C₁₋₆) alkylamino.

Aryl includes naphthyl, anthracyl, fluorenyl and indenyl but is preferably phenyl.

The term heteroaryl refers to an aromatic ring containing up to 10 atoms including one or more heteroatoms (preferably one or two heteroatoms) selected from O, S and N. Examples of such rings include pyridine, pyrimidine, furan, quinoline, quinazoline, pyrazole, thiophene, thiazole, oxazole and isoxazole.

The terms heterocycle and heterocyclyl refer to a non-aromatic ring containing up to 10 atoms including one or more (preferably one or two) heteroatoms selected from O, S and N. Examples of such rings include 1,3-dioxolane, tetrahydrofuran and morpholine.

When present, the optional substituents on heterocyclyl include C₁₋₆ alkyl as well as those optional substituents given above for an alkyl moiety.

Cycloalkyl includes cyclopropyl, cyclopentyl and cyclohexyl.

Cycloalkenyl includes cyclopentenyl and cyclohexenyl.

When present, the optional substituents on heteroaryl and aryl rings are selected, independently, from halogen, nitro, cyano, NCS—, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy-(C₁₋₆)alkyl, C₂₋₆ alkenyl, C₂₋₆ haloalkenyl, C₂₋₆ alkynyl, C₃₋₇ cycloalkyl (itself optionally substituted with C₁₋₆ alkyl or halogen), C₅₋₇ cycloalkenyl (itself optionally substituted with C₁₋₆ alkyl or halogen), hydroxy, C₁₋₁₀alkoxy, C₁₋₁₀ alkoxy(C₁₋₁₀)alkoxy, tri(C₁₋₄)alkyl-silyl(C₁₋₆)alkoxy, C₁₋₆ alkoxycarbonyl(C₁₋₁₀)alkoxy, C₁₋₁₀ haloalkoxy, aryl(C₁₋₄)alkoxy (where the aryl group is optionally substituted), C₃₋₇ cycloalkyloxy (where the cycloalkyl group is optionally substituted with C₁₋₆ alkyl or halogen), C₁₋₁₀alkenyloxy, C₁₋₁₀ alkynyloxy, SH, C₁₋₁₀alkylthio, C₁₋₁₀ haloalkylthio, aryl(C₁₋₄)alkylthio (where the aryl group may be further optionally substituted), C₃₋₇ cycloalkylthio (where the cycloalkyl group is optionally substituted with C₁₋₆ alkyl or halogen), tri(C₁₋₄)alkylsilyl(C₁₋₆)alkylthio, arylthio (where the aryl group is optionally substituted), C₁₋₆ alkylsulfonyl, C₁₋₆ haloalkylsulfonyl, C₁₋₆ alkylsulfinyl, C₁₋₆ haloalkylsulfinyl, arylsulfonyl (where the aryl group is optionally substituted), tri(C₁₋₄)alkylsilyl, aryldi(C₁₋₄)alkylsilyl, (C₁₋₄)alkyldiarylsilyl, triarylsilyl, C₁₋₁₀alkylcarbonyl, HO₂C, C₁₋₁₀alkoxycarbonyl, aminocarbonyl, C₁₋₆ alkylaminocarbonyl, di(C₁₋₆ alkyl)aminocarbonyl, N-(C₁₋₃ alkyl)-N-(C₁₋₃ alkoxy)aminocarbonyl, C₁₋₆ alkylcarbonyloxy, arylcarbonyloxy (where the aryl group is optionally substituted), di(C₁₋₆)alkylamino-carbonyloxy, aryl (itself optionally substituted), heteroaryl (which itself may be further optionally substituted), heterocyclyl (itself optionally substituted with C₁₋₆ alkyl or halogen), aryloxy (where the aryl group is optionally substituted), heteroaryloxy (where the heteroaryl group is optionally substituted), heterocyclyloxy (where the heterocyclyl group is optionally substituted with C₁₋₆ alkyl or halogen), amino, C₁₋₆ alkylamino, di(C₁₋₆)alkylamino, C₁₋₆ alkylcarbonylamino and N-(C₁₋₆)alkylcarbonyl-N-(C₁₋₆)alkylamino.

For substituted phenyl and heteroaryl moieties it is preferred that one or more substituents are independently selected from halogen, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy(C₁₋₆)alkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, C₁₋₆ alkylthio, C₁₋₆ haloalkylthio, C₁₋₆ alkylsulfinyl, C₁₋₆ haloalkylsulfinyl, C₁₋₆ alkylsulfonyl, C₁₋₆ haloalkylsulfonyl, C₂₋₆ alkenyl, C₂₋₆ haloalkenyl, C₂₋₆ alkynyl, C₃₋₇ cycloalkyl, nitro, cyano, CO₂H, C₁₋₆ alkylcarbonyl, C₁₋₆ alkoxycarbonyl, R₃₃R₃₄N or R₃₅R₃₆NC(O); wherein R₃₃, R₃₄, R₃₅ and R₃₆ are, independently, hydrogen or C₁₋₆ alkyl.

In the context of the specification the term halogen is fluorine, bromine, iodine or preferably chlorine; similarly haloalkyl is preferably C₁-C₆-alkyl, more preferably lower alkyl, that is linear or branched and is substituted by one or more, for example in the case of halo-ethyl up to five, halogen atoms, especially fluorine (an example is trifluoromethyl.

Haloalkoxy is preferably C₁-C₆-alkoxy, more preferably lower alkoxy, that is linear or branched and that is substituted by one or more, for example in the case of haloethyl up to five, halogen atoms, especially fluorine; trifluoromethoxy and 1,1,2,2-tetrafluoroethoxy are especially preferred.

The moiety attached to the 2-position of the pyridine ring in the compounds of the invention, namely the moiety

includes 5- and 6-membered ring systems, which are common in the art of heterocycles. Thus examples of the moieties include 2,4-dihydro-pyrazol-3-ones, 2,4-dihydro-pyrazole-3-thione, 1H-pyrazoles, 2H-pyridazin-3-ones, 4,5-dihydro-2H-pyridazin-3-ones, 1,2-dihydro-pyrazol-3-ones, 1,2-dihydro-pyrazole-3-thione, pyrazolidin-3-one, pyrazolidine-3-thione, 2H-pyridazin-3-thione and 4,5-dihydro-2H-pyridazin-3-thione.

More preferred ring systems for the moiety positioned at the 2-position of the pyridyl ring are those selected from the group comprising, 1H-pyrazoles, 2,4-dihydro-pyrazol-3-ones, 1,2-dihydro-pyrazol-3-ones, 4,5-dihydro-2H-pyridazin-3-ones.

The compounds of formula I can form acid addition salts, for example with inorganic acids, such as hydrochloric acid, sulfuric acid or a phosphoric acid, or with suitable organic carboxylic or sulfonic acids, for example aliphatic mono- or di-carboxylic acids, such as trifluoroacetic acid, acetic acid, propionic acid, glycolic acid, succinic acid, maleic acid, fumaric acid, hydroxymaleic acid, malic acid, tartaric acid, citric acid, oxalic acid or amino acids, such as arginine or lysine, aromatic carboxylic acids, such as benzoic acid, 2-phenoxy-benzoic acid, 2-acetoxy-benzoic acid, salicylic acid, 4-aminosalicylic acid, aromatic-aliphatic carboxylic acids, such as mandelic acid or cinnamic acid, heteroaromatic carboxylic acids, such as nicotinic acid or isonicotinic acid, aliphatic sulfonic acids, such as methane-, ethane- or 2-hydroxy-ethane-sulfonic acid, or aromatic sulfonic acids, for example benzene-, p-toluene- or naphthalene-2-sulfonic acid.

The pyridine-N-oxides of formula I can form acid addition salts with strong acids, such as hydrochloric acid, nitric acid, phosphoric acid or sulfonic acids, such as benzenesulfonic acid.

Formula I according to the invention shall include all the possible isomeric forms, as well as mixtures, e.g. racemic mixtures, and any mixtures of rotamers.

In view of the close relationship between the compounds of formula I in free form and in the form of their salts, including also salts that can be used as intermediates, for example in the purification of the compounds of formula I or in order to identify those compounds, herein-before and hereinafter any reference to the (free) compounds is to be understood as including also the corresponding salts, where appropriate and expedient.

Among the compounds of formula I according to the present invention the following groups of compounds are preferred. These groups are in any combination those

-   wherein -   n is 0; -   p is 0 or 1; -   m is 1, 2 or 3 or m is 1 and R₁ is preferably at the 3- or     4-position of the phenyl ring, preferably at the 3-position. -   R₁ is selected from the group comprising halogen, C₁₋₃ haloalkoxy,     CH(OH)R, COR, SO₂NRR′, CH(NR′R″)R, COORa or CONRbRc where Ra, Rb,     Rc, R, R′, R″ are independently H or lower alkyl or -   R₁ is selected from the group comprising chlorine, fluorine,     trifluoromethyl, trifluoromethoxy, or 1,1,2,2-tetrafluoroethoxy, or -   R₁ is 3-chloro; -   R₂ is selected from the group comprising hydrogen, methyl, ethyl,     methoxy, methoxymethyl, ethoxymethyl, or -   R₂ is selected from the group comprising hydrogen, methyl or methoxy     or -   R₂ is methyl or -   the ring members CR₂R_(2A) are a carbonyl group (C═O) or a     thiocarbonyl group (C═S); -   R_(2A) is selected from the group comprising hydrogen, methyl,     ethyl, methoxymethyl, ethoxymethyl, or -   R_(2A) is hydrogen, methyl, or R_(2A) forms a bond together with R₈; -   R₃ and R₄ are independently selected from the group comprising     hydrogen, methyl, ethyl, hydroxy, trifluoromethyl, methoxy,     methoxymethyl, ethoxymethyl, or -   R₃ and R₄ are independently selected from the group comprising     hydrogen methyl or methoxy or -   R₃ and R₄ are independently hydrogen or methyl or the ring members     CR₃R₄ are a carbonyl group (C═O) or a thiocarbonyl group (C═S); or -   R₄ together with either R₉ or R₈ forms a bond; -   R₅, R₆, R₇, R₈ are each independently hydrogen, methyl,     trifluoromethyl, -   R₆ and R₇ may also be independently chloro, methoxy, ethoxy,     diethylamine -   R₇ may also be formyl or -   the groups R₇ and R₈ together with the carbon atom to which they are     attached form a cyclopropyl ring or -   R₅ together with R₈ form a bond or -   R₅, R₆, R₇, R₈ are each independently hydrogen, methyl; -   R₉ is hydrogen or methyl; -   R₁₀ is hydrogen, methyl, ethyl, allyl, propargyl, methoxymethyl,     thiomethoxymethyl or ethoxymethyl, or -   R₁₀ is hydrogen or methoxymethyl.

In a further group of preferred compounds R₂, R_(2A), R₃, R₄, R₅, R₆, R₇, R₈ and R₉ independently of each other are hydrogen or methyl;

-   -   In a further group of preferred compounds R₇ is hydrogen,         methyl, ethyl, allyl, propargyl, methoxymethyl,         thiomethoxymethyl or ethoxymethyl, more preferably hydrogen or         methoxymethyl.

Preferred individual compounds of the formula I are:

-   (3-Chloro-phenyl)-(4-[2-(3,4,5-trimethyl-pyrazol-1-yl)-pyridin-4-yl]-pyrimidin-2-yl)-amine; -   (3-Chloro-phenyl)-{4-[2-(5-methoxy-3-methoxymethyl-pyrazol-1-yl)-pyridin-4-yl]-pyrimidin-2-yl)-amine; -   (3-Chloro-phenyl)-{4-[2-(5-methoxy-3-methoxymethyl-4-methyl-pyrazol-1-yl)-pyridin-4-yl]-pyrimidin-2-yl}-amine; -   (3-Chloro-phenyl)-(4-[2-(5-methoxy-4-methyl-pyrazol-1-yl)-pyridin-4-yl]-pyrimidin-2-yl}-amine;     (3-Chloro-phenyl)-{4-[2-(5-ethoxy-3,4-dimethyl-pyrazol-1-yl)-pyridin-4-yl]-pyrimidin-2-yl}-amine; -   2-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-5-methoxymethyl-1,4-dimethyl-1,2-dihydro-pyrazol-3-one; -   2-(4-{2-[(3-Chloro-phenyl)-methoxymethyl-amino]-pyrimidin-4-yl}-pyridin-2-yl)-1,5-dimethyl-1,2-dihydro-pyrazol-3-one; -   2-{4-[2-(3-Chloro-phenylamino)-pyridin-4-yl]-pyridin-2-yl}-1-ethyl-4,5-dimethyl-1,2-dihydro-pyrazol-3-one; -   2-{4-[2-(3-Chloro-phenylamino)-pyridin-4-yl]-pyridin-2-yl}-1,4-dimethyl-1,2-dihydro-pyrazol-3-one; -   2-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-1,5-dimethyl-1,2-dihydro-pyrazol-3-one; -   2-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-5-methoxymethyl-4,4-dimethyl-2,4-dihydro-pyrazol-3-one;     2-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-4,4-dimethyl-2,4-dihydro-pyrazol-3-one; -   2-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}4,4,5-trimethyl-2,4-dihydro-pyrazole-3-thione; -   5-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-7-methyl-5,6-diaza-spiro[2.4]hept-6-en-4-one; -   2-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-4-ethyl-4,5-dimethyl-2,4-dihydro-pyrazol-3-one; -   (3-Chloro-phenyl)-{4-[2-(5-methoxy-3-methyl-pyrazol-1-yl)-pyridin-4-yl]-pyrimidin-2-yl}-amine; -   2{-4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-1,4,5-trimethyl-1,2-dihydro-pyrazol-3-one; -   2-{4-(3-Chloro-phenylamino)-pyridin-4-yl-pyridin-2-yl}-4,4,5-trimethyl-2,4-dihydro-pyrazol-3-one; -   2-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-1,5-dimethyl-1,2-dihydro-pyrazol-3-one; -   4,5-Dichloro-2-{4-[2-(3-chloro-phenylamino)-pyridin-4-yl]-pyridin-2-yl}-2H-pyridazin-3-one; -   2-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-6-methyl-2H-pyridazin-3-one; -   2-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-6-methyl-4,5-dihydro     2H-pyridazin-3-one; -   2-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-6-Phenyl-4,5-dihydro-2H-pyridazin-3-one; -   4-Chloro-2-{4-[2-(3-chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-5-ethoxy-2H-pyridazin-3-one; -   4-Chloro-2-{4-[2-(3-chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-5-ethylsulfanyl-2H-pyridazin-3-one; -   5-Azido-4-chloro-2-{4-[2-(3-chloro-phenylamino)-pyridin-4-yl]-pyridin-2-yl}-2H-pyridazin-3-one; -   1-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-2-methyl-pyrazolidin-3-one; -   (3-Chloro-phenyl)-{4-[2-(5-methoxy-3,4-dimethyl-pyrazol-1-yl)-pyridin-4-yl]-pyrimidin-2-yl}-amine; -   2-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-5-methoxymethyl-1-methyl-1,2-dihydro-pyrazol-3-one; -   2-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-1,5-dimethyl-3-oxo-2,3-dihydro-1H-pyrazole-4-carbaldehyde; -   5-Chloro-2-{4-[2-(3-chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-4-(oxetan-3-yloxy)-2H-pyridazin-3-one;     and -   4-Chloro-2-{4-[2-(3-chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-5-(tetrahydro-furan-2-ylmethoxy)-2H-pyridazin-3-one.

The compounds according to the invention may be prepared according to methods per se known in the art (this does mean, however, that, where novel compounds are produced, the respective process of manufacture is also novel). The procedures for the preparation of compounds of formula I may be outlined as follows:

-   A) reacting a compound of the formula (II)     (or a salt thereof) with β-ketoester of the formula III to V under     acid catalysed conditions     wherein R is H or optionally substituted alkyl and the other     moieties in II to V have the meanings given for a compound of     formula I thus obtaining a compound of the sub-formula Ia

Compounds of formula II may be prepared by the methods described in WO 01/93682 and illustrated in Synthesis Example 1.

B) reacting a compound of subformula Ia with a thionating reagent such as for example Lawesson reagent to obtain a compound of subformula Ib

C) compounds of sub-formula Ia and Ib can be mono- or bis-alkylated to form compounds of structure I wherein p is 0 and all the other moieties have the meanings given for a compound of formula I D) reacting a compound of the formula II (or a salt thereof)

with a substituted acrylate of formula VI

or with an alkyl propiolate of formula VII

thus obtaining a compound of subformula Ic wherein the moieties have the meanings given for a compound of formula I

E) Conversion of the C═O group into the corresponding C═S group in subformula Ic can be achieved by reacting Ic with a thionating reagent such as e.g. Lawesson reagent thus producing compounds of subformula Id

F) compounds of subformula Ic and Id can be alkylated to form compounds of structure I wherein p is 0, R3 is optionally substituted alkoxy or optionally substituted alkylthio and all the other moieties have the meanings given for a compound of formula I

G) reacting a compound of the formula II (or a salt thereof)

with a substituted 1,3 dicarbonyl compound of formula VIII

H) reacting a compound of the formula II (or a salt thereof)

with a 1,4 dicarbonyl compounds of formula 1× or X wherein R is H or optionally substituted alkyl

I) reacting a compound of the formula I.6 (or a salt thereof)

With a nucleophile to form compounds of formula I

Compounds of forumla I.6 are prepared by the methods of W Davey and D J Tivey, J Chem Soc 1958, p1230 and illustrated in Example 7.

J) reacting a compound of the formula XI (or a salt thereof) with a cyclic hydrazine system of formula XII in the presence of a base and a metal catalyst, such as palladium(II) or palladium(0) complexes commonly used for Buchwald-Hartwig aminations

The R group moieties in compounds VIII, IX, X, XI and XII are as for those defined for compounds of formula I.

Compounds of formula HI to XII inclusive are known compounds or may be prepared by compounds known processes.

The reaction types A to J and additional methods which can be applied per se or as analogous procedures for the synthesis of compounds of formula I are described for example in:

For 5-membred heterocylces:

-   J. Bernstein; et al.; J. Am. Chem. Soc. 1947, 69, 1157; -   H. Priewe, A. Poljak; Chem. Ber. 1955, 88, 1932; -   Patent Application CH 77-10606 19770831 (1982); -   EP0680954A2;

For 6 membred heterocycles

-   Francis, John E.; Doebel, Karl. J.; Schutte, Paula M. Bachmann,     Ernst F. Can. J. Chem. 1982, 60, 1214-1232. Sauter, Fritz; Stanetty,     Peter; Blaschke, Alfred; Vyplel, Hermann J. Chem Miniprint, 4, 1981,     1087-1096. Mikhailovskii, A. Chem. Hetreocycl. Compd. (Engl.     Trans.), 1998, 34, 2, 163-166. J. Med. Chem. 1999, 42, 6, 1088-1099.     Krutosikova, Alzbeta; Dandarova, Miloslava; Konecny, Vaclav;     Collect.Czech.Chem.Commun.; EN; 55; 11; 1990; 2707-2714. Benjamin,     Louis E. Earley James V. Gilman Normnan W. J. Heterocyclic. Chem.     1986, 23, 119-124. Patent, Chem. Fabr. Schering, DE 406214. Gregory;     Wiggins; J.Chem.Soc.; 1949; 2546, 2549. Lancelot, Jean-Charles;     Robba, Max; Chem.Pharm.Bull. 36; 7; 1988; 2381-2385.     Example on Phenylhydrazine: Bourel, Line; Tartar, Andre; Melnyk,     Patricia; TELEAY; Tetrahedron Lett.; 37; 24; 1996; 41454148.     Sawhney, S. N., Bhutani Sanjay, Vir, Indian J.Chem.Sect.B; 26, 5;     1987, 348-350. P. Coudert, J. Couquelet, P. Tronche J. of     Heterocyclic. Chem. 1988, 25, 799.     The chloro atoms of formula 1.6 can be substituted by aryl groups     under palladium catalysed conditions according to procedures     described in: Bert U. W. Maes, Omar 'kyek, Janez Komrlj, Guy L. F.     Lemiére, Eddy Esmans, Jef Rozenski, Roger A. Dommisse and Achiel     Haemers Tetrahedron, 2001, 57(7), 1323-1330.     β-Ketoesters of formula III-V are known or can be prepared according     to procedures described in: -   Hyoung R. K. Synlett 1998, 789-791; Freskos J. N. Tetrahedron     letters, Vol. 35, No. 6, pp. 835-838 (1994); -   J. Chem. Soc., Perkin Trans. 1, (4), 839-61 (1988); Bull. Soc. Chim.     Belg., 94(7), 449-56 (1985); -   Collins D. J. Aust. J. Chem., 43, 617-22 (1990);     -   Procedures for the alkylation of compounds of the subformula Ia         to Id are described in the experimental section using Williamson         conditions.         Conversion of C═O groups (in Ia and Ic) into C═S groups         (subformulas Ib and Id) is described in the experimental section         using Lawesson reagent under standard conditions or according to         procedures given in         Ley, Steven V.; Leach, Andrew G.; Storer, R. Ian. J. Chem. Soc.,         Perkin Trans. 1 (2001), (4), 358-361.

Procedures for the palladium catalysed C—N linkage reaction (Burchwald-Hartwig amination) of compounds of formula XI with cyclic hydrazine ring systems of formula XII are given in the experimental part and are described in PCT/IBO1/02821.

EXAMPLES

The subsequent examples are intended to illustrated the invention, without however limiting the scope thereof.

Synthesis Example 1 (3-Chloro-phenyl)-[4-(2-hydrazino-pyridin-4-yl)-pyrimidin-2-yl]-amine

A mixture of (3-chloro-phenyl)-[4-(2-chloro-pyridin-4-yl)-pyrimidin-2-yl]-amine (4.8 g, 0.015 mol) in hydrazine (20 ml, 0.41 mol) is refluxed for 90 minutes. The reaction is poured into ethanol (300 ml) with efficient stirring. The resulting precipitate is filtered with suction to yield the title compound, m.p. 201-203° C.

Synthesis Example 2 2-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-5-methyl-2.4-dihydro-pyrazol-3-one

A mixture of (3-Chloro-phenyl)-[4-(2-hydrazino-pyridin-4-yl)-pyrimidin-2-yl]-amine (3.14 g, 0.010 mol) and Methyl acetoacetate (1.28 g, 0.010 mol) in EtOH (30 ml) and Acetic acid (30 ml) is stirred at reflux for one hour. At room temperature the resulting precipitate is filtered with suction to yield the title compound,(3.50 g, 92%) m.p. 149-150° C.

Synthesis Example 3

A mixture of 2-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-5-methyl-2,4-dihydro-pyrazol-3-one (3.42 g, 0.009 mol), iodomethane (2.52 g, 0.018 mol) and potassium carbonate anhydrous (3.78 g, 0.027 mol) in DMF (30 ml) is stirred at room temperature for three hours. After stirring the resulting is partitioned between ethyl acetate and water. The organic phase is separated, dried over magnesium sulfate, filtered and evaporated under reduced pressure. The residue is purified twice by silicagel chromatography to give all possible Isomers of the title compounds llla to lllf. llla (0.10 g, 2.8%) m.p. 185-188° C.,

-   lllb (0.29 g, 8.1%) m.p. 163-166° C., -   lllc (0.52 g, 14.1%) m.p. 192-194° C., -   llld (0.53 g, 14.4%) m.p. 89-94° C., -   llle (0.29 g, 8.0%) m.p. 149-150° C., -   lllf (0.11 g, 3.0%) m.p. 149-150° C.,

Synthesis Example llla 2-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl 1-4,5-dimethyl-2,4-dihydro-pyrazol-3-one

Synthesis Example lllb 2-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-4,4,5-trimethyl-2,4-dihydro-pyrazol-3-one

Synthesis Example lllc 2-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-1,4,5-dimethyl-1,2-dihydro-pyrazol-3-one

Synthesis Example llld 2-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-1,4,5-trimethyl-1,2-dihydro-pyrazol-3-one

Synthesis Example llle (3-Chloro-phenyl)-f 4-[2-(5-methoxy-3-methyl-pyrazol-1-yl)-pyridin-4-yl]-pyrimidin-2-yl}-amine

Synthesis Example lllf (3-Chloro-phenyl)-{4-[2-(5-methoxy-3,4-dimethyl-pyrazol-1-yl)-pyridin-4-yl]-pyrimidin-2-yl}-amine

Synthesis Example 4 Synthesis Example lVb 2-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-4,4,5-trimethyl-2,4-dihydro-pyrazole-3-thione

A mixture of 2-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-4,4,5-trimethyl-2,4-dihydro-pyrazol-3-one (0.21 g, 0.0005 mol) and Lawesson reagent (0.22 g 0.0005 mol) in toluene (3 ml) is stirred at 100° C. for one hour. After cooling the resulting solution is directly purified by silicagel column chromatography to the title compounds (lVb) (0.19 g, 88.1%) m.p. 167-168° C.,

Synthesis Example 5 Synthesis Example V 1-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-4,5-dihydro-1H-pyrazol-3-ol

To a mixture of (3-Chloro-phenyl)-[4-(2-hydrazino-pyridin-4-yl)-pyrimidin-2-yl]-amine (7.82 g, 0.025 mol) and Methyl acrylate (2.58 g, 0.030 mol) in tert BuOH (80 ml) is added Potassium tert-butoxyde (5.6 g, 0.05 mol) in portions at 25° C. After stirring for two hours the resulting brown solution is poured in water (500 ml), acidified with acetic acid and partitioned between ethyl acetate and water. The organic phase is separated, dried over magnesium sulfate, filtered and evaporated under reduced pressure. The residue is purified by crystallizing from acetone. The resulting precipitate is filtered with suction to yield the title compound. (1.55 g, 16.9%) m.p. 222-226° C.

Synthesis Example 6

A mixture of 1-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-4,5-dihydro-1H-pyrazol-3-ol (0.734 g, 0.0020 mol), iodomethane (175 μl, 0.0028 mol) and potassium carbonate anhydrous (0.497 g, 0.0036 mol) in acetonitrile (4 ml) and DMF (2 ml) is stirred at 45° C. for seven hours. After stirring the resulting is partitioned between ethyl acetate and water. The organic phase is separated, dried over magnesium sulfate, filtered and evaporated under reduced pressure. The residue is purified by silicagel chromatography to give both possible Isomers of the title compounds.

Vla (0.192 g, 25.2%) mp. 143-144° C.

Vlb (0.036 g, 4.7%) mp. 202-205° C.

Synthesis Example Vla 1-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-2-methyl-pyrazolidin-3-on

Synthesis Example Vlb (3-Chloro-phenyl)-{4-[2-(3-methoxy-4,5-dihydro-pyrazol-1-yl)-pyridin-4-yl]-pyrimidin-2-yl}-amine

Synthesis Example 7 4,5-Dichloro-2-{4-[2-(3-chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-2H-pyridazin-3-one

To a suspension of (3-Chloro-phenyl)-[4-(2-hydrazino-pyridin-4-yl)-pyrimidin-2-yl]-amine (5 g) in acetic acid (80 mL) was added 2.8 g of Mucochloric acid. The mixture was heated at 125° C. for 4 h. The solvent was concentrated and the crude was poured into water (500 mL). The suspension was neutralised by addition of solid potassium carbonate until pH 7. The aqueous phase was extracted with ethyl acetate (3×200 mL). The organic phases were combined, dried over MgSO₄, and concentrated. Flash silica chromatography, eluting with ethyl acetate-tetrahydrofuran (1-0 to 1-1), afforded the title compound as a solid (3.11 g, 44%). Mp 238-240° C., 1H NMR (DMSO-d6) 10.3 (1H, s, NW, 8.84 (1H, d, 5 Hz), 8.76 (1H, d, 5 Hz), 8.42 (1H, s), 8.38(1H, s), 8.28 (1H, dd, 2 Hz, 5 Hz), 8.04(1H, t, 2 Hz), 7.74(1H, dd), 7.62(1H, d, 5 Hz), 7.32(1H, t, 8 Hz), 7.02(1H, dd, 2 Hz, 8 Hz). 13CNMR DMSO-d6) 160.3, 160.2, 159.9, 155.5, 153.5, 150.2, 146.6, 141.7, 136.7, 136.6, 134.0, 132.9, 130.1, 121.9, 121.1, 118.7, 118.2, 117.3, 109.3.

Synthesis Example 8 2-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-6-methyl-2H-pyridazin-3-one

To a suspension of (3-Chloro-phenyl)-[4-(2-hydrazino-pyridin-4-yl)-pyrimidin-2-yl]-amine (2 g) in acetic acid (40 nL) was acetate (3×200 mL).). The organic phase were combined, dried over MgSO4, and concentrated. Flash silica chromatography, eluting with ethyl acetate-tetrahydrofuran (1-0 to 1-1), afforded the title compound as a solid (1.39 g, 55%). Mp 187-189° C., 1H NMR (DMSO-d6) 9.8 (1H, s, NH), 8.86 (1H, d, 5 Hz), 8.80 (1H, d, 5 Hz), 8.35 (1H, s), 8.28(1H, dd, 2 Hz, 5 Hz), 8.14 (1H, t, 2 Hz), 7.73 (1H, m), 7.7.48(1H, d, 10 Hz), 7.36(1H, t, 8 Hz), 7.14(1H, d, 10 Hz), 7.08(1H, dd, 1 Hz, 7 Hz), 2.39 (3H,s), 13CNMR (DMSO-d6) 160.8, 160.5, 160.3, 159.0, 154.8, 150.5, 146.7, 145.4, 142.2, 135.4, 133.3, 130.8, 130.5, 121.5, 119.2, 118.6, 117.7, 109.6, 20.58.

Synthesis Example 9 2-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-6-methyl-4,5-dihydro-2H-pyridazin-3-one

To a suspension of (3-Chloro-phenyl)-[4-(2-hydrazino-pyridin-4-yl)-pyrimidin-2-yl]-amine (2 g) in n-Butanol (40 nL) was added of 0.744 g of levulinic acid. The mixture was heated at reflux. After 3 h, the mixture was cooled at 0° C. and the 4-({4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-hydrazono)-4-methyl-butyric acid (1.92 g, 73%) was recovered by filtration. Mp 218-220° C., 1H NMR DMSO-d6) 12.1 (1H, OHacid), 9.93 (1H, s, NH), 9.48 (1H, s, NH), 8.64 (1H, d, 5 Hz), 8.24 (1H, d, 5 Hz), 8.0 (1H, s), 7.76 (2H, m), 7.46 (1H, d, 5 Hz), 7.38 (1H, dd, 2 Hz, 5 Hz), 7.30 (1H, t, 8 Hz), 6.98 (1H, dd, 1 Hz, 8 Hz), 2.51 (4H, s), 1.92 (3H, s), ¹³C NMR (DMSO-d6 176.2, 164.6, 161.6, 161.2, 150.5, 150.1, 147.5, 144.0, 134.9, 132.1, 122.97, 120.13, 119.2, 113.7, 111.1, 105.9, 35.33 (CH2), 32.56(CH2), 18.09 (CH3), MS (ES−) 409 (M−1, 100), 819 (2M−1, 30). The 4-({4-[2-(3-Chloro-phenylamino)-pyrimnidin-4-yl]-pyridin-2-yl}-hydrazono)-4-methyl-butyric acid (1.5 g) was dissolved in acetic acid (40 mL). The solution was stirred at 110° C. for 3 h then the solution was poured in a mixture of water and ice (250 mL) and neutralised with a solution saturated of sodium hydrogenocarbonate until pH 7. The mixture was extracted with ethyl acetate (3×100 mL). The organic phase were combined, dried over MgSO4, and concentrated. Flash silica chromatography, eluting with ethyl acetate-tetrahydrofuran (3-1), afforded the title compound as a solid (0.7263 g, 51%). Mp 189-192° C., 1H NMR (DMSO-d6) 10.07(1H, NH), 8.73 (1H, d, 5 Hz), 8.69 (1H, d, 5 Hz), 8.16 (1H, s), 8.06 (2H, m), 7.73 (1H, dd, 3 Hz, 10 Hz), 7.60(1H, d, 5 Hz), 7.31 (1H, t, 8 Hz), 7.03(1H, dd, 3 Hz, 8 Hz), 2.63 (4H, m), 2.07 (3H, s). ¹³C NMR (DMSO-d6) 165.3, 160.3, 159.6, 159.3, 154.9, 153.9, 149.0, 141.1, 132.5, 129.7, 120.7, 119.2, 117.8, 117.6, 116.7, 108.66, 26.4, 25.3, 22.0. MS (ES+) 393 (MH+, 100), 785 (2 MH+, 60).

Synthesis Example 10 2-{(4[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-6-Phenyl-4,5-dihydro-2H-pyridazin-3-one

To a suspension of (3-Chloro-phenyl)-[4-(2-hydrazino-pyridin-4-yl)-pyrimidin-2-yl]-amine (2 g) in n-Butanol (40 mL) was added of 1.14 g of 3-benzoylpropionic acid. The mixture was heated at reflux. After 3 h, the mixture was cooled at 0° C. and the 4-({4[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-hydrazono)-4-phenyl-butyric acid (2.19 g, 72%) was recovered by filtration. Mp 144-146° C., 1H NMR (DMSO-d6).12.0 (1H, OH), 10.4 (1H, s, NH), 10.1 (1H, s, NH), 8.77 (1H, d, 5 Hz), 8.42 (1H, d, 5 Hz) 8.12 (1H, s), 8.06(1H, s), 7.80(3H, m), 7.6 (1H, d, 5 Hz) 7.53 (1H, d, 5 Hz), 7.45 (3H, m), 7.34 (1H, t, 8 Hz), 7.08 (1H, m) 3.4 (2H, m), 2.95 (2H, m), MS (ES+) 473 (MH+, 100),. MS (ES−) 471 (M−1, 100). To a solution of 4-({4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-hydrazono)-4-phenyl-butyric acid (0.48 g) in tetrahydrofuranne (40 mL) was additionned N,N′-dicyclohexylcarbodiimide (0.23 g) and 1-Hydroxybenzotriazole (0.1401 g). The solution was stirred at reflux for 2 h then the solvent was evaporated. The crude was chromatographied, eluting with ethyl acetate to gave the title compound as a solid (0.3366 g, 78%). Mp 165-167° C., 1H NMR (CDCl₃) 9.6 (1H,s, NH), 8.76 (1H, d, 5 Hz), 8.59 (1H, d, 5 Hz), 8.21 (1H, s), 7.86 (4H, m), 7.44 (4H, m), 7.26(2H, m), 7.01 (1H, m), 3.18 (2H, t, 8 Hz), 2.87 (2H, t, 8 Hz). 13C NMR (CDCl₃) 166.3, 162.4, 160.4, 159.8, 154.8, 152.9, 150.1, 146.7, 140.9, 135.7, 134.9, 130.5, 130.3, 129.0, 126.7, 122.9, 120.1, 119.6, 118.8, 117.55, 109.6, 28.4, 23.6. MS (ES+) 455 (MH+, 100), 909 (2 MH+, 10).

Synthesis Example 11 4-Chloro-2-{4-[2-(3-chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-5-ethoxy-2H-pyridazin-3-one

To a suspension of 4,5-Dichloro-2-{4-[2-(3-chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-2H-pyridazin-3-one (0.3 g) in ethanol (10 mL) was added of 0.220 mg of potassium carbonate. The mixture was heated to reflux for 4 h. The suspension was poured into water (50 mL) and extracted with ethyl acetate (2×100 mL). The organic phase were combined, dried over MgSO₄, and concentrated. Flash silica chromatography, eluting with ethyl acetate-hexane (9:1), afforded the title compound as a solid (0.130 g, 35%). Mp 196-198° C., 1H NMR (CDCl₃) 8.80 (1H, d, 3 Hz), 8.60 (1H, d, 6 Hz), 8.42 (1H, s), 8.02 (2H, d, m), 7.93 (1H, s), 7.46 (1H, dd, 6 Hz, 3 Hz), 7.31 (1H,m), 7.29(1H, d, 3 Hz), 7.28(1H, s), 4.43 (2H, q, 6 Hz), 1.56 (3H, t, 6 Hz).

Synthesis Example 12 4-Chloro-2-{4-[2-(3-chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-5-ethylsulfanyl-2H-pyridazin-3-one

To a suspension of 4,5-Dichloro-2-{4-[2-(3-chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-2H-pyridazin-3-one (0.3 g) in acetonitrile (10 mL) was added of 0.15 mL of ethylmercaptan and 0.280 mg of potassium carbonate. The mixture was heated to reflux for 2 h. The suspension was filtered and the solid was washed with ethyl acetate to gave the title compound (0.220 g, 46%).Mp 80-100° C., 1H NMR (DMSO-d6) 8.8 (1H, d, 3 Hz), 859 (1H, d, 6 Hz), 8.37 (1H, s, NH), 7.98 (1H, d, 6 Hz, 3 Hz), 7.92 (1H, t, 3 Hz), 7.86 (1H, s), 7.46 (1H, d, 9 Hz, 3 Hz), 7.40 (1H,s), 7.27(2H, m), 7.04(1H, d, 9 Hz), 3.12 (2H, q, 6 Hz), 1.47 (3H, t, 6 Hz).

Synthesis Example 13 5-Azido-4-chloro-2-{4-[2-(3-chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-2H-pyridazin-3-one

To a suspension of 4,5-Dichloro-2-{4-[2-(3-chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-2H-pyridazin-3-one (0.3 g) in acetonitrile (10 mL) was added of 0.09 g of sodium azide. The mixture was heated to reflux for 4 h. The suspension was filtered to give the title compound as a solid (0.280 g, 95%). Mp 184-186° C., 1H NMR (DMSO-d6) 10.1 (1H, s, NH), 8.75 (1H, d, 6 Hz), 8.67 (1H, d, 3 Hz), 8.28 (1H, s), 8.27 (1H, s), 8.18(1H, dd, 1 Hz, 3 Hz), 7.97 (1H, m), 7.65 (1H,dd), 7.57(1H, d, 6 Hz), 7.25(1H, t, 9 Hz), 6.94 (1H, dd).

Synthesis Example 14 5-Chloro-4-cyclopropylamin-2-{4-[2-(3-chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-2H-pyridazin-3-one and 5-Cyclopropylamin-4-chloro-2-{4-[2-(3-chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl)-2H-pyridazin-3-one

A suspension of 4,5-Dichloro-2-{4-[2-(3-chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-2H-pyridazin-3-one (0.3 g) in cyclopropylamine (10 mL) was heated at reflux for 2 h. The solvent was evaporated under vacuum. Flash silica chromatography, eluting with ethyl acetate-hexane (1:1), afforded the 5-Chloro-4-cyclopropylamin-2-{4-[2-(3-chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-2H-pyridazin-3-one as a solid (Mp 117-121° C., 0.082 g, 26%) and the 5-cyclopropylamin-4-chloro-2-{4-[2-(3-chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-2H-pyridazin-3-one (Mp 90-100° C., 0.180 g, 58%) as a solid.

Synthesis Example 15 5-Chloro-4-butanol-2-(4-[2-(3-chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-2H-pyridazin-3-one

To a solution of butanol (0.18 mL) in tetrahydrofuran (40 mL) was added a solution of Lithium diisopropylamide (1.5 M, 1.3 mL) at room temperature. The solution was stirred for 15 minutes followed by the addition of 4,5-Dichloro-2-{4-[2-(3-chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-2H-pyridazin-3-one (0.7 g). The mixture was heated at 85° C. for 1 h. The suspension was poured into brine (200 mL) and extracted with ethyl acetate (3×100 mL). The organic phase were combined, dried over MgSO4, and concentrated under vacuum. Flash silica chromatography, eluting with ethyl acetate-cyclohexane (1:1), afforded the title compound as a solid (0.4128 g, 55%). Mp 118-127° C.

Synthesis Example 16 1-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-2-methyl-tetrahydro-pyridazine-3,6-dione

To a solution of succinic anhydride (2.16 g) in chloroform (60 mL) 1.16 mL of methyl hydrazine were added at room temperature. The solution was stirred 2 h at room temperature then heated at reflux for 1 h. The solvent was evaporated. 1 g of the obtained solid was dissolved in tetrahydrofuran (10 mL) followed by the addition of 1.55 g of N,N′-dicyclohexylcarbodiimide and 1.01 g of 1-hydroxybenzotriazole. The mixture was heated at reflux for 1 h. The mixture was cooled to 0° C. and a solution of oxalic acid (0.617 g) in methanol was added. The suspension was filtered and the solvent was evaporated. Flash silica chromatography, eluting with ethyl acetate-methanol (5%), afforded the 1-Methyl-tetrahydro-pyridazine-3,6-dione as a solid (0.4128 g, 24%). 0.014 g of Pd(dba)3 and xantphos (0.018 g) were dissolved in toluene (2 mL). The mixture was stirred at room temperature for 20 minutes. Then the 1-Methyl-tetrahydro-pyridazine-3,6-dione, the (3-Chloro-phenyl)-[4-(2-chloro-pyridin-4-yl)-pyrimidin-2-yl]-amine (0.2 g) and sodium terbutanolate (0.085 g) were added. The mixture was heated at reflux for 2 h. The suspension was poured into water (50 mL) and extracted with ethyl acetate (3×100 mL). The organic phase was separated, dried over MgSO4, filtered and concentrated. Flash silica chromatography, eluting with ethyl acetate, afforded the title compound as a solid (0.169 g, 65%). Mp 201-204° C.

The compounds in the following Tables further illustrate the invention TABLE 1 Compounds of the general structure I.1 wherein R₁ to R₁₀, m, n, and p correspond with a line of table A and B1 I.1

TABLE 2 Compounds of the general structure I.2 wherein R₁ to R₁₀, m, n, and p correspond with a line of table A and B2 I.2

TABLE 3 Compounds of the general structure I.3 wherein R₁ to R₁₀, m, n, and p correspond with a line of table A and B3 I.3

TABLE 4 Compounds of the general structure I.4 wherein R₁ to R₁₀, m, n, and p correspond with a line of table A and B4 I.4

TABLE 5 Compounds of the general structure I.5 wherein R₁ to R₁₀, m, n, and p correspond with a line of table A and B5 I.5

TABLE 6 Compounds of the general structure I.6 wherein R₁ to R₁₀, m, n, and p correspond with a line of table A and B6 I.6

TABLE 7 Compounds of the general structure I.7 wherein R1 to R10, m, n, and p correspond with a line of table A and B7 I.7

TABLE 8 Compounds of the general structure I.8 wherein R1 to R10, m, n, and p correspond with a line of table A and B8 I.8

Compounds of general structure I are any combination of the definitions given in Table A and the appropriate Table B, wherein n, R₁₀, m and R₁ correspond with a line of Table A and wherein R₂-R₉ and p correspond with a line of the appropriate Table B. TABLE A No. n R₁₀ 2-R₁ 3-R₁ 4-R₁ 5-R₁ 6-R₁ 001 0 CH₃ H OH H H F 002 0 CH₃ H OH H F H 003 0 CH₃ CH₃ H H H H 004 0 CH₃ H Cl H H F 005 0 CH₃ H Cl H H CH₃ 006 0 CH₃ H CH₃ Cl H H 007 0 CH₃ F H Cl H H 008 0 CH₃ H Cl H H H 009 0 CH₃ H C(O)H H H H 010 0 CH₃ H CH₂OH H H H 011 0 CH₃ H CH(OH)CH₃ H H H 012 0 CH₃ H F H H H 013 0 CH₃ H CH₃ H H H 014 0 CH₃ H H H CF₃ H 015 0 CH₃ H H H OCF₃ H 016 0 CH₃ H N(CH₃)₂ H H F 017 0 CH₃ H SO₂N(CH₃)₂ H H H 018 0 CH₃ H H H CONH₂ H 019 0 CH₃ H H H OCH₂CΞCH H 020 0 CH₃ H SC₄H₉ H H H 021 0 H H OH H F H 022 0 H H OH H H F 023 0 H CH₃ H H H H 024 0 H H Cl H H F 025 0 H H Cl H H CH₃ 026 0 H H CH₃ Cl H H 027 0 H F H Cl H H 028 0 H H Cl H H H 029 0 H H C(O)H H H H 030 0 H H CH₂OH H H H 031 0 H H CH(OH)CH₃ H H H 032 0 H H F H H H 033 0 H H CH₃ H H H 034 0 H H H H CF₃ H 035 0 H H H H OCF₃ H 036 0 H H N(CH₃)₂ H H F 037 0 H H SO₂N(CH₃)₂ H H H 038 0 H H H H CONH₂ H 039 0 H H H H OCH₂CΞCH H 040 0 H H SC₄H₉ H H H 041 0 CH₂OCH₃ H OH H H F 042 0 CH₂OCH₃ H OH H F H 043 0 CH₂OCH₃ CH₃ H H H H 044 0 CH₂OCH₃ H Cl H H F 045 0 CH₂OCH₃ H Cl H H CH₃ 046 0 CH₂OCH₃ H CH₃ Cl H H 047 0 CH₂OCH₃ F H Cl H H 048 0 CH₂OCH₃ H Cl H H H 049 0 CH₂OCH₃ H C(O)H H H H 050 0 CH₂OCH₃ H CH₂OH H H H 051 0 CH₂OCH₃ H CH(OH)CH₃ H H H 052 0 CH₂OCH₃ H F H H H 053 0 CH₂OCH₃ H CH₃ H H H 054 0 CH₂OCH₃ H H H CF₃ H 055 0 CH₂OCH₃ H H H OCF₃ H 056 0 CH₂OCH₃ H N(CH₃)₂ H H F 057 0 CH₂OCH₃ H SO₂N(CH₃)₂ H H H 058 0 CH₂OCH₃ H H H CONH₂ H 059 0 CH₂OCH₃ H H H OCH₂CΞCH H 060 0 CH₂OCH₃ H SC₄H₉ H H H 061 0 CH₂OCH₃ H OH H H F 062 0 CH₂OCH₃ H Cl H H H 063 0 CH₂OCH₃ H C(O)H H H H 064 0 CH₂OCH₃ H CH₂OH H H H 065 0 CH₂OCH₃ H CH(OH)CH₃ H H H 066 0 CH₂OCH₃ H F H H H 067 0 CH₂OCH₃ H CH₃ H H H 068 0 CH₂OCH₃ H H H CF₃ H 069 0 CH₂OCH₃ H H H OCF₃ H 070 0 CH₂OCH₃ H N(CH₃)₂ H H F 071 0 CH₂OCH₃ H SO₂N(CH₃)₂ H H H 072 0 CH₂OCH₃ H H H CONH₂ H 073 0 CH₂SCH₃ H OH H H F 074 0 CH₂SCH₃ H Cl H H H 075 0 CH₂SCH₃ H C(O)H H H H 076 0 CH₂SCH₃ H CH₂OH H H H 077 0 CH₂SCH₃ H CH(OH)CH₃ H H H 078 0 CH₂SCH₃ H F H H H 079 0 CH₂SCH₃ H CH₃ H H H 080 0 CH₂SCH₃ H H H CF₃ H 081 0 CH₂SCH₃ H H H OCF₃ H 082 0 CH₂SCH₃ H N(CH₃)₂ H H F 083 0 CH₂SCH₃ H SO₂N(CH₃)₂ H H H 084 0 CH₂SCH₃ H H H CONH₂ H 085 0 CH₂CH═CH₂ H OH H H F 086 0 CH₂CH═CH₂ H Cl H H H 087 0 CH₂CH═CH₂ H C(O)H H H H 088 0 CH₂CH═CH₂ H CH₂OH H H H 089 0 CH₂CH═CH₂ H CH(OH)CH₃ H H H 090 0 CH₂CH═CH₂ H F H H H 091 0 CH₂CH═CH₂ H CH₃ H H H 092 0 CH₂CH═CH₂ H H H CF₃ H 093 0 CH₂CH═CH₂ H H H OCF₃ H 094 0 CH₂CH═CH₂ H N(CH₃)₂ H H F 095 0 CH₂CH═CH₂ H SO₂N(CH₃)₂ H H H 096 0 CH₂CH═CH₂ H H H CONH₂ H 097 0 CH₂CΞCH H OH H H F 098 0 CH₂CΞCH H Cl H H H 099 0 CH₂CΞCH H C(O)H H H H 100 0 CH₂CΞCH H CH₂OH H H H 101 0 CH₂CΞCH H CH(OH)CH₃ H H H 102 0 CH₂CΞCH H F H H H 103 0 CH₂CΞCH H CH₃ H H H 104 0 CH₂CΞCH H H H CF₃ H 105 0 CH₂CΞCH H H H OCF₃ H 106 0 CH₂CΞCH H N(CH₃)₂ H H F 107 0 CH₂CΞCH H SO₂N(CH₃)₂ H H H 108 0 CH₂CΞCH H H H CONH₂ H 109 0 CH₂CΞCH H OH H H F 110 0 CH₂Ph H Cl H H H 111 0 CH₂Ph H C(O)H H H H 112 0 CH₂Ph H CH₂OH H H H 113 0 CH₂Ph H CH(OH)CH₃ H H H 114 0 CH₂Ph H F H H H 115 0 CH₂Ph H CH₃ H H H 116 0 CH₂Ph H H H CF₃ H 117 0 CH₂Ph H H H OCF₃ H 118 0 CH₂Ph H N(CH₃)₂ H H F 119 0 CH₂Ph H SO₂N(CH₃)₂ H H H 120 0 H H Cl CH₃ H H 121 0 H H Cl CH₃ H H 122 0 H H Cl OCH₃ H H 123 0 H H F H F H 124 0 H H Cl H Cl H 125 0 H H Br H H H

TABLE B-1 I.1

No. R₂ R_(2A) R₃ R₇ R₈ R₉ 01 C═O CH₃ CH₃ CH₃ 02 C═S CH₃ CH₃ H 03 C═O CH₃ CH₃ CH₂CH₃ 04 C═O CH₃ CH₂—CH₂ 05 C═O CH₃ CH₃ Ph 06 C═S CH₃ CH₃ CH₃ 07 C═O H CH₃ CH₃ 08 C═O CH₂OCH₃ CH₃ CH₃ 09 C═O CH₃ CH₃ CH₂Ph 010 C═O CH₃ CH₂CH₂OC(O)CH₃ H 011 C═O CH₃ CO₂Et H 012 C═O CH₃ CHO H 013 C═O CH₃ CF₃ H 014 C═O CF₃ CF₃ H 015 C═O CF₃ H H 016 C═O CH₂CH₃ H H 017 C═O CH₂CH₃ CH₃ H 018 C═O n-C₄H₉ CH₃ H 019 C═O Ph CH₃ H 020 C═S n-C₄H₉ CH₃ H 021 C═S CH₃ CH₃ CH₂—CH₃ 022 C═S CH₃ CH₂—CH₂ 023 C═S CH₃ CH₃ Ph 024 C═S H CH₃ CH₃ 025 C═S CH2OCH3 CH₃ CH₃ 026 C═S CH₃ CH₃ CH₂Ph 027 C═S CH₃ CH₂CH₂OC(O)CH₃ H 028 C═S CH₃ CO₂Et H 029 C═S CH₃ CHO H 030 C═S CH₃ CF₃ H 031 C═S CF₃ CF₃ H 032 C═S CF₃ H H 033 C═S CH₂CH₃ H H 034 C═S CH₂CH₃ CH₃ H 035 C═S Ph CH₃ H 036 C═O CH₃ CO₂Et CH₃ 037 C═O CH₃ CHO CH₃ 038 C═O CH₃ CF₃ CH₃ 039 C═O CF₃ CF₃ CH₃ 040 C═O CF₃ CH₃ H 041 C═O CH₂CH₃ CF₃ H 042 C═O CH₂CH₃ CH₃ H 043 C═S CH₃ CO₂Et CH₃ 044 C═S CH₃ CHO CH₃ 045 C═S CH₃ CF₃ CH₃ 046 C═S CF₃ CF₃ CH₃ 047 C═S CF₃ CH₃ H 048 C═S CH₂CH₃ CF₃ H 049 C═S CH₂CH₃ CH₃ H 050 H H OCH₃ H H 051 H H OCH₂Ph H H 052 H H OCH₂CCH H H 053 H H

H H

TABLE B-2 I.2

No. R₂ R_(2A) R₃ R₇ R₉ 01 C═O CH₃ C(O)₂Me CH₃ 02 C═O CH₃ CH₃ CH₃ 03 C═O CH₃ H CH₃ 04 C═O CH₃ CHO CH₃ 05 C═O H CH₃ CH₃ 06 C═O CH₃ CH₃ CH₂—CH₃ 07 C═O CH₃ CH₃ CH₂PH 08 C═O CH₃ H CH₃ 09 C═O CH₂OCH₃ CH₃ CH₃ 010 C═O CH₃ CH₃ Ac 011 C═O CH₂OCH₃ H CH₃ 012 C═S CH₃ H CH₃ 013 C═S CH₃ C(O)₂Me CH₃ 014 C═S CH₃ CH₃ CH₃ 015 C═S CH₃ CHO CH₃ 016 C═S H CH₃ CH₃ 017 C═S CH₃ CH₃ CH₂—CH₃ 018 C═S CH₃ CH₃ CH₂PH 019 C═S CH₃ H CH₃ 020 C═S CH₂OCH₃ CH₃ CH₃ 021 C═S CH₃ CH₃ Ac 022 C═S CH₂OCH₃ H CH₃ 023 C═O CH₂Ph CH₃ CH₃ 024 C═O n-C₄H₉ CH₃ CH₃ 025 C═O CH₂CH₃ CH₃ CH₂CH₃ 026 C═O CH₂CH₃ CH₃ CH₃ 027 C═O CF₃ n-C₄H₉ CH₃ 028 C═O CH₂Ph H CH₃ 029 C═O n-C₄H₉ H CH₃ 030 C═O CH₂CH₃ CH₂Ph CH₂CH₃ 031 C═O CH₂CH₃ H CH₃ 032 C═O CF₃ CH₃ CH₃ 033 C═S CH₂Ph CH₃ CH₃ 034 C═S n-C₄H₉ CH₃ CH₃ 035 C═S CH₂CH₃ CH₃ CH₂CH₃ 036 C═S CH₂CH₃ CH₃ CH₃ 037 C═S CF₃ n-C₄H₉ CH₃ 038 C═S CH₂Ph H CH₃ 039 C═S n-C₄H₉ H CH₃ 040 C═S CH₂CH₃ CH₂Ph CH₂CH₃ 041 C═S CH₂CH₃ H CH₃ 042 C═S CF₃ CH₃ CH₃

TABLE B-3 I.3

No. R₂ R₃ R₇  01 OCH3 CH₃ H  02 Oac CH₃ CH₃  03 OC₂H₅ CH₃ CH₃  04 OC₂H₅ H CH₃  05 OC₂H₅ CH₃ H  06 OC₂H₅ H Ph  07 OC₂H₅ CH₂OCH₃ CH₃  08 OC₂H₅ CH₂OCH₃ CH₂CH₃  09 OH CH₂OCH₃ CH₃ 010 OH CH₂OCH₃ CH₂CH₃ 011 OH CH₂OCH₃ H 012 OCH3 H CH₃ 013 OCH3 CH₂OCH₃ CH₃ 014 OCH3 CH₂OCH₃ H 015 OH CH₃ CH₂CH₃ 016 OH H CH₃ 017 CH₃ CH₃ CH₃ 018 OAc CH₃ H 019 OH CH₃ H 020 OCH₂Ph CH₃ CH₃ 021 SCH3 CH₃ CH₃ 022 SCH3 CH₃ CH₂CH₃ 023 SCH3 CH₃ H 024 SCH3 CH₃ CH₂CH₃ 025 SCH3 H H 026 SCH3 H CH₃ 027 CH₃ CH₃ 028 CH₃ CH₃ CH₃ 029 CH₃ CH₃ C(O)₂Et 030 CH(CH₃)₂ CH(CH₃)₂ H 031 CH₃ CH₃ Cl 032 H OCH3 H 033 CH₂OCH₃ H C(O)₂Me 034 CH₂OCH₃ H CONHMe 035 c-C₃H₅ CH₃ H 036 I—C₃H₇ CH₃ C(O)₂Et 037 CH₃ CH₃ Ph 038 CH₃ CF₃ H 039 H OH H 040 2,4-F₂-Ph C(O)₂Me H 041 2,4-F₂-Ph CONHMe H 042 SCH3 CH₂OCH₃ CH₃ 043 SCH3 CH₂OCH₃ H 044 SH CH₃ CH₂CH₃ 045 SH H CH₃ 046 SCH3 CH₃ H 047 SCH₂Ph CH₃ CH₃ 048 SC₂H₅ CH₃ CH₃ 049 SC₂H₅ H CH₃ 050 SC₂H₅ CH₃ H 051 SC₂H₅ H Ph 052 SC₂H₅ CH₂OCH₃ CH₃ 053 SC₂H₅ CH₂OCH₃ CH₂CH₃

TABLE B-4 I.4

No. R₂ R₃ R₄ R₇ R₉  01 H C═O H CH₃  02 H C═O H

 03 H C═O H Benzyl  04 H C═O H CH₂CΞCH  05 CH₃ C═O H CH₃  06 CH₃ C═O H CH₂CH₃  07 CH₃ C═O H n-C₄H₉  08 CH₃ C═O H CH₂Ph  09 CH₂CH₃ C═O H CH₃ 010 CH₂CH₃ C═O H CH₃ 011 Ph C═O H CH₃ 012 Ph C═O H CH₂CH₃ 013 Ph C═O H Ph 014 Ph C═O H n-C₄H₉ 015 H C═S H CH₃ 016 H C═S H Benzyl 017 H C═S H CH₂CΞCH 018 CH₃ C═S H CH₃ 019 CH₃ C═S H CH₂CH₃ 020 CH₃ C═S H n-C₄H₉ 021 CH₃ C═S H CH₂Ph 022 CH₂CH₃ C═S H CH₃ 023 CH₂CH₃ C═S H CH₃ 024 Ph C═S H CH₃ 025 Ph C═S H CH₂CH₃ 026 Ph C═S H Ph 027 Ph C═S H n-C₄H₉

TABLE B-5 I.5

No. R₂ R_(2A) R₃ R₄ R₇ R₈ R₉  01 H H C═O H H CH₃  02 H H C═O H H

 03 H H C═O H H Benzyl  04 H H C═O H H CH₂CΞCH  05 CH₃ H C═O CH₃ H CH₂Ph  06 CH₃ H C═O CH₃ H CH₂CΞCH  07 CH₃ H C═O CH₃ H CH₂CH═CH₂  08 CH₃ H C═O CH₃ H CH₃  09 CH₃ H C═O CH₃ H CH₂CH₃ 010 CH₃ H C═O H H CH₂Ph 011 CH₃ H C═O H H CH₂CΞCH 012 CH₃ H C═O H H CH₂CH═CH₂ 013 CH₃ H C═O H H CH₃ 014 CH₃ H C═O H H CH₂CH₃ 015 CH₃ CH₃ C═O H H CH₂Ph 016 CH₃ CH₃ C═O H H CH₂CΞCH 017 CH₃ CH₃ C═O H H CH₂CH═CH₂ 018 CH₃ CH₃ C═O H H CH₃ 019 CH₃ CH₃ C═O H H CH₂CH₃ 020 CH₃ H C═S H H CH₂Ph 021 CH₃ H C═S H H CH₂CΞCH 022 CH₃ H C═S H H CH₂CH═CH₂ 023 CH₃ H C═S H H CH₃ 024 CH₃ H C═S H H CH₂CH₃ 025 CH₃ CH₃ C═S H H CH₂Ph 026 CH₃ CH₃ C═S H H CH₂CΞCH 027 CH₃ CH₃ C═S H H CH₂CH═CH₂ 028 CH₃ CH₃ C═S H H CH₃ 029 CH₃ CH₃ C═S H H CH₂CH₃ 030 C═O H H H H CH₃

TABLE B-6 I.6

R₃ R₆ R₇   1. H H H   2. H Cl Cl   3. H Cl NHCH₃   4. H Cl NHBu   5. H Cl N(CH₃)₂   6. H Cl NBu₂   7. H Cl NCH₃Bu   8. H Cl NEt₂   9. H Cl NEtBu  10. H Cl SCH₃  11. H Cl SBu  12. H Cl OCH₃  13. H Cl OBu  14. H Cl CF₃  15. H Cl OPh  16. H Cl CH₂OCH₃  17. H Cl OCF₃  18. H Cl OCF₂CF₃  19. H Cl Ph  20. H Cl N₃  21. H H I  22. H H CH₃  23. H H Bu  24. H H OCH₃  25. H H OBu  26. H H SCH₃  27. H H SBu  28. H H NHCH₃  29. H H NHBu  30. H H N(CH₃)₂  31. H H NBu₂  32. H H NCH₃Bu  33. H H NEt₂  34. H H NEtBu  35. H H CF₃  36. H H OPh  37. H H CH₂OCH₃  38. H H OCF₃  39. H H OCF₂CF₃  40. H H Ph  41. H H N₃  42. H CH₃ CH₃  43. H CH₃ Bu  44. H CH₃ OCH₃  45. H CH₃ OBu  46. H CH₃ SCH₃  47. H CH₃ SBu  48. H CH₃ NHCH₃  49. H CH₃ NHBu  50. H CH₃ N(CH₃)₂  51. H CH₃ NBu₂  52. H CH₃ NCH₃Bu  53. H CH₃ NEt₂  54. H CH₃ NEtBu  55. H CH₃ CF₃  56. H CH₃ OPh  57. H CH₃ CH₂OCH₃  58. H CH₃ OCF₃  59. H CH₃ OCF₂CF₃  60. H CH₃ Ph  61. H CH₃ N₃  62. H nBu CH₃  63. H nBu Bu  64. H nBu OCH₃  65. H nBu OBu  66. H nBu SCH₃  67. H nBu SBu  68. H nBu NHCH₃  69. H nBu NHBu  70. H nBu N(CH₃)₂  71. H nBu NBu₂  72. H nBu NCH₃Bu  73. H nBu NEt₂  74. H nBu NEtBu  75. H nBu CF₃  76. H nBu OPh  77. H nBu CH₂OCH₃  78. H nBu OCF₃  79. H nBu OCF₂CF₃  80. H nBu Ph  81. H nBu N₃  82. H I H  83. H CH₃ H  84. H Bu H  85. H OCH₃ H  86. H OBu H  87. H SCH₃ H  88. H SBu H  89. H NHCH₃ H  90. H NHBu H  91. H N(CH₃)₂ H  92. H NBu₂ H  93. H NCH₃Bu H  94. H NEt₂ H  95. H NEtBu H  96. H CF₃ H  97. H OPh H  98. H CH₂OCH₃ H  99. H OCF₃ H 100. H OCF₂CF₃ H 101. H Ph H 102. H N₃ H 103. H CH₃ CH₃ 104. H Bu CH₃ 105. H OCH₃ CH₃ 106. H OBu CH₃ 107. H SCH₃ CH₃ 108. H SBu CH₃ 109. H NHCH₃ CH₃ 110. H NHBu CH₃ 111. H N(CH₃)₂ CH₃ 112. H NBu₂ CH₃ 113. H NCH₃Bu CH₃ 114. H NEt₂ CH₃ 115. H NEtBu CH₃ 116. H CF₃ CH₃ 117. H OPh CH₃ 118. H CH₂OCH₃ CH₃ 119. H OCF₃ CH₃ 120. H OCF₂CF₃ CH₃ 121. H Ph CH₃ 122. H N₃ CH₃ 123. H CH₃ nBu 124. H nBu nBu 125. H OCH₃ nBu 126. H OBu nBu 127. H SCH₃ nBu 128. H SBu nBu 129. H NHCH₃ nBu 130. H NHBu nBu 131. H N(CH₃)₂ nBu 132. H NBu₂ nBu 133. H NCH₃Bu nBu 134. H NEt₂ nBu 135. H NEtBu nBu 136. H CF₃ nBu 137. H OPh nBu 138. H CH₂OCH₃ nBu 139. H OCF₃ nBu 140. H OCF₂CF₃ nBu 141. H Ph nBu 142. H N₃ nBu 143. H NHCH₃ Cl 144. H NHBu Cl 145. H N(CH₃)₂ Cl 146. H NBu₂ Cl 147. H NCH₃Bu Cl 148. H NEt₂ Cl 149. H NEtBu Cl 150. H SCH₃ Cl 151. H SBu Cl 152. H OCH₃ Cl 153. H OBu Cl 154. H CF₃ Cl 155. H OPh Cl 156. H CH₂OCH₃ Cl 157. H OCF₃ Cl 158. H OCF₂CF₃ Cl 159. H Ph Cl 160. H N₃ Cl 161. H NHCH₃ NHCH₃ 162. H NHBu NHBu 163. H N(CH₃)₂ N(CH₃)₂ 164. H NBu₂ NBu₂ 165. H NCH₃Bu NCH₃Bu 166. H NEt₂ NEt₂ 167. H NEtBu NEtBu 168. H SCH₃ SCH₃ 169. H SBu SBu 170. H OCH₃ OCH₃ 171. H OBu OBu 172. H CF₃ CF₃ 173. H OPh OPh 174. H CH₂OCH₃ CH₂OCH₃ 175. H OCF₃ OCF₃ 176. H OCF₂CF₃ OCF₂CF₃ 177. H Ph Ph 178. H N₃ N₃ 179. CH₃ H H 180. CH₃ Cl Cl 181. CH₃ Cl NHCH₃ 182. CH₃ Cl NHBu 183. CH₃ Cl N(CH₃)₂ 184. CH₃ Cl NBu₂ 185. CH₃ Cl NCH₃Bu 186. CH₃ Cl NEt₂ 187. CH₃ Cl NEtBu 188. CH₃ Cl SCH₃ 189. CH₃ Cl SBu 190. CH₃ Cl OCH₃ 191. CH₃ Cl OBu 192. CH₃ Cl CF₃ 193. CH₃ Cl OPh 194. CH₃ Cl CH₂OCH₃ 195. CH₃ Cl OCF₃ 196. CH₃ Cl OCF₂CF₃ 197. CH₃ Cl Ph 198. CH₃ Cl N₃ 199. CH₃ H I 200. CH₃ H CH₃ 201. CH₃ H Bu 202. CH₃ H OCH₃ 203. CH₃ H OBu 204. CH₃ H SCH₃ 205. CH₃ H SBu 206. CH₃ H NHCH₃ 207. CH₃ H NHBu 208. CH₃ H N(CH₃)₂ 209. CH₃ H NBu₂ 210. CH₃ H NCH₃Bu 211. CH₃ H NEt₂ 212. CH₃ H NEtBu 213. CH₃ H CF₃ 214. CH₃ H OPh 215. CH₃ H CH₂OCH₃ 216. CH₃ H OCF₃ 217. CH₃ H OCF₂CF₃ 218. CH₃ H Ph 219. CH₃ H N3 220. CH₃ CH₃ CH₃ 221. CH₃ CH₃ Bu 222. CH₃ CH₃ OCH₃ 223. CH₃ CH₃ OBu 224. CH₃ CH₃ SCH₃ 225. CH₃ CH₃ SBu 226. CH₃ CH₃ NHCH₃ 227. CH₃ CH₃ NHBu 228. CH₃ CH₃ N(CH₃)₂ 229. CH₃ CH₃ NBu₂ 230. CH₃ CH₃ NCH₃Bu 231. CH₃ CH₃ NEt₂ 232. CH₃ CH₃ NEtBu 233. CH₃ CH₃ CF₃ 234. CH₃ CH₃ OPh 235. CH₃ CH₃ CH₂OCH₃ 236. CH₃ CH₃ OCF₃ 237. CH₃ CH₃ OCF₂CF₃ 238. CH₃ CH₃ Ph 239. CH₃ CH₃ N₃ 240. CH₃ nBu CH₃ 241. CH₃ nBu Bu 242. CH₃ nBu OCH₃ 243. CH₃ nBu OBu 244. CH₃ nBu SCH₃ 245. CH₃ nBu SBu 246. CH₃ nBu NHCH₃ 247. CH₃ nBu NHBu 248. CH₃ nBu N(CH₃)₂ 249. CH₃ nBu NBu₂ 250. CH₃ nBu NCH₃Bu 251. CH₃ nBu NEt₂ 252. CH₃ nBu NEtBu 253. CH₃ nBu CF₃ 254. CH₃ nBu OPh 255. CH₃ nBu CH₂OCH₃ 256. CH₃ nBu OCF₃ 257. CH₃ nBu OCF₂CF₃ 258. CH₃ nBu Ph 259. CH₃ nBu N3 260. CH₃ I H 261. CH₃ CH₃ H 262. CH₃ Bu H 263. CH₃ OCH₃ H 264. CH₃ OBu H 265. CH₃ SCH₃ H 266. CH₃ SBu H 267. CH₃ NHCH₃ H 268. CH₃ NHBu H 269. CH₃ N(CH₃)₂ H 270. CH₃ NBu₂ H 271. CH₃ NCH₃Bu H 272. CH₃ NEt₂ H 273. CH₃ NEtBu H 274. CH₃ CF₃ H 275. CH₃ OPh H 276. CH₃ CH₂OCH₃ H 277. CH₃ OCF₃ H 278. CH₃ OCF₂CF₃ H 279. CH₃ Ph H 280. CH₃ N₃ H 281. CH₃ CH₃ CH₃ 282. CH₃ Bu CH₃ 283. CH₃ OCH₃ CH₃ 284. CH₃ OBu CH₃ 285. CH₃ SCH₃ CH₃ 286. CH₃ SBu CH₃ 287. CH₃ NHCH₃ CH₃ 288. CH₃ NHBu CH₃ 289. CH₃ N(CH₃)₂ CH₃ 290. CH₃ NBu₂ CH₃ 291. CH₃ NCH₃Bu CH₃ 292. CH₃ NEt₂ CH₃ 293. CH₃ NEtBu CH₃ 294. CH₃ CF₃ CH₃ 295. CH₃ OPh CH₃ 296. CH₃ CH₂OCH₃ CH₃ 297. CH₃ OCF₃ CH₃ 298. CH₃ OCF₂CF₃ CH₃ 299. CH₃ Ph CH₃ 300. CH₃ N₃ CH₃ 301. CH₃ CH₃ nBu 302. CH₃ Bu nBu 303. CH₃ OCH₃ nBu 304. CH₃ OBu nBu 305. CH₃ SCH₃ nBu 306. CH₃ SBu nBu 307. CH₃ NHCH₃ nBu 308. CH₃ NHBu nBu 309. CH₃ N(CH₃)₂ nBu 310. CH₃ NBu₂ nBu 311. CH₃ NCH₃Bu nBu 312. CH₃ NEt₂ nBu 313. CH₃ NEtBu nBu 314. CH₃ CF₃ nBu 315. CH₃ OPh nBu 316. CH₃ CH₂OCH₃ nBu 317. CH₃ OCF₃ nBu 318. CH₃ OCF₂CF₃ nBu 319. CH₃ Ph nBu 320. CH₃ N₃ nBu 321. CH₃ NHCH₃ Cl 322. CH₃ NHBu Cl 323. CH₃ N(CH₃)₂ Cl 324. CH₃ NBu₂ Cl 325. CH₃ NCH₃Bu Cl 326. CH₃ NEt₂ Cl 327. CH₃ NEtBu Cl 328. CH₃ SCH₃ Cl 329. CH₃ SBu Cl 330. CH₃ OCH₃ Cl 331. CH₃ OBu Cl 332. CH₃ CF₃ Cl 333. CH₃ OPh Cl 334. CH₃ CH₂OCH₃ Cl 335. CH₃ OCF₃ Cl 336. CH₃ OCF₂CF₃ Cl 337. CH₃ Ph Cl 338. CH₃ N₃ Cl 339. CH₃ NHCH₃ NHCH₃ 340. CH₃ NHBu NHBu 341. CH₃ N(CH₃)₂ N(CH₃)₂ 342. CH₃ NBu₂ NBu₂ 343. CH₃ NCH₃Bu NCH₃Bu 344. CH₃ NEt₂ NEt₂ 345. CH₃ NEtBu NEtBu 346. CH₃ SCH₃ SCH₃ 347. CH₃ SBu SBu 348. CH₃ OCH₃ OCH₃ 349. CH₃ OBu OBu 350. CH₃ CF₃ CF₃ 351. CH₃ OPh OPh 352. CH₃ CH₂OCH₃ CH₂OCH₃ 353. CH₃ OCF₃ OCF₃ 354. CH₃ OCF₂CF₃ OCF₂CF₃ 355. CH₃ Ph Ph 356. CH₃ N₃ N₃ 357. nBu H H 358. nBu Cl Cl 359. nBu Cl NHCH₃ 360. nBu Cl NHBu 361. nBu Cl N(CH₃)₂ 362. nBu Cl NBu₂ 363. nBu Cl NCH₃Bu 364. nBu Cl NEt₂ 365. nBu Cl NEtBu 366. nBu Cl SCH₃ 367. nBu Cl SBu 368. nBu Cl OCH₃ 369. nBu Cl OBu 370. nBu Cl CF₃ 371. nBu Cl OPh 372. nBu Cl CH₂OCH₃ 373. nBu Cl OCF₃ 374. nBu Cl OCF₂CF₃ 375. nBu Cl Ph 376. nBu Cl N₃ 377. nBu H I 378. nBu H CH₃ 379. nBu H Bu 380. nBu H OCH₃ 381. nBu H OBu 382. nBu H SCH₃ 383. nBu H SBu 384. nBu H NHCH₃ 385. nBu H NHBu 386. nBu H N(CH₃)₂ 387. nBu H NBu₂ 388. nBu H NCH₃Bu 389. nBu H NEt₂ 390. nBu H NEtBu 391. nBu H CF₃ 392. nBu H OPh 393. nBu H CH₂OCH₃ 394. nBu H OCF₃ 395. nBu H OCF₂CF₃ 396. nBu H Ph 397. nBu H N₃ 398. nBu CH₃ CH₃ 399. nBu CH₃ Bu 400. nBu CH₃ OCH₃ 401. nBu CH₃ OBu 402. nBu CH₃ SCH₃ 403. nBu CH₃ SBu 404. nBu CH₃ NHCH₃ 405. nBu CH₃ NHBu 406. nBu CH₃ N(CH₃)₂ 407. nBu CH₃ NBu₂ 408. nBu CH₃ NCH₃Bu 409. nBu CH₃ NEt₂ 410. nBu CH₃ NEtBu 411. nBu CH₃ CF₃ 412. nBu CH₃ OPh 413. nBu CH₃ CH₂OCH₃ 414. nBu CH₃ OCF₃ 415. nBu CH₃ OCF₂CF₃ 416. nBu CH₃ Ph 417. nBu CH₃ N₃ 418. nBu nBu CH₃ 419. nBu nBu Bu 420. nBu nBu OCH₃ 421. nBu nBu OBu 422. nBu nBu SCH₃ 423. nBu nBu SBu 424. nBu nBu NHCH₃ 425. nBu nBu NHBu 426. nBu nBu N(CH₃)₂ 427. nBu nBu NBu₂ 428. nBu nBu NCH₃Bu 429. nBu nBu NEt₂ 430. nBu nBu NEtBu 431. nBu nBu CF₃ 432. nBu nBu OPh 433. nBu nBu CH₂OCH₃ 434. nBu nBu OCF₃ 435. nBu nBu OCF₂CF₃ 436. nBu nBu Ph 437. nBu nBu N3 438. nBu I H 439. nBu CH₃ H 440. nBu Bu H 441. nBu OCH₃ H 442. nBu OBu H 443. nBu SCH₃ H 444. nBu SBu H 445. nBu NHCH₃ H 446. nBu NHBu H 447. nBu N(CH₃)₂ H 448. nBu NBu₂ H 449. nBu NCH₃Bu H 450. nBu NEt₂ H 451. nBu NEtBu H 452. nBu CF₃ H 453. nBu OPh H 454. nBu CH₂OCH₃ H 455. nBu OCF₃ H 456. nBu OCF₂CF₃ H 457. nBu Ph H 458. nBu N₃ H 459. nBu CH₃ CH₃ 460. nBu Bu CH₃ 461. nBu OCH₃ CH₃ 462. nBu OBu CH₃ 463. nBu SCH₃ CH₃ 464. nBu SBu CH₃ 465. nBu NHCH₃ CH₃ 466. nBu NHBu CH₃ 467. nBu N(CH₃)₂ CH₃ 468. nBu NBu₂ CH₃ 469. nBu NCH₃Bu CH₃ 470. nBu NEt₂ CH₃ 471. nBu NEtBu CH₃ 472. nBu CF₃ CH₃ 473. nBu OPh CH₃ 474. nBu CH₂OCH₃ CH₃ 475. nBu OCF₃ CH₃ 476. nBu OCF₂CF₃ CH₃ 477. nBu Ph CH₃ 478. nBu N₃ CH₃ 479. nBu CH₃ nBu 480. nBu nBu nBu 481. nBu OCH₃ nBu 482. nBu OBu nBu 483. nBu SCH₃ nBu 484. nBu SBu nBu 485. nBu NHCH₃ nBu 486. nBu NHBu nBu 487. nBu N(CH₃)₂ nBu 488. nBu NBu₂ nBu 489. nBu NCH₃Bu nBu 490. nBu NEt₂ nBu 491. nBu NEtBu nBu 492. nBu CF₃ nBu 493. nBu OPh nBu 494. nBu CH₂OCH₃ nBu 495. nBu OCF₃ nBu 496. nBu OCF₂CF₃ nBu 497. nBu Ph nBu 498. nBu N₃ nBu 499. nBu NHCH₃ Cl 500. nBu NHBu Cl 501. nBu N(CH₃)₂ Cl 502. nBu NBu₂ Cl 503. nBu NCH₃Bu Cl 504. nBu NEt₂ Cl 505. nBu NEtBu Cl 506. nBu SCH₃ Cl 507. nBu SBu Cl 508. nBu OCH₃ Cl 509. nBu OBu Cl 510. nBu CF₃ Cl 511. nBu OPh Cl 512. nBu CH₂OCH₃ Cl 513. nBu OCF₃ Cl 514. nBu OCF₂CF₃ Cl 515. nBu Ph Cl 516. nBu N₃ Cl 517. nBu NHCH₃ NHCH₃ 518. nBu NHBu NHBu 519. nBu N(CH₃)₂ N(CH₃)₂ 520. nBu NBu₂ NBu₂ 521. nBu NCH₃Bu NCH₃Bu 522. nBu NEt₂ NEt₂ 523. nBu NEtBu NEtBu 524. nBu SCH₃ SCH₃ 525. nBu SBu SBu 526. nBu OCH₃ OCH₃ 527. nBu OBu OBu 528. nBu CF₃ CF₃ 529. nBu OPh OPh 530. nBu CH₂OCH₃ CH₂OCH₃ 531. nBu OCF₃ OCF₃ 532. nBu OCF₂CF₃ OCF₂CF₃ 533. nBu Ph Ph 534. nBu N₃ N₃ 535. Ph H H 536. Ph CH₃ CH₃ 537. Ph CH₃ H 538. Ph H CH₃ 539. CH₂OCH₃ H H 540. CH₂OCH₃ CH₃ CH₃ 541. CH₂OCH₃ CH₃ H 542. CH₂OCH₃ H CH₃ 543. CF₃ H H 544. CF₃ CH₃ CH₃ 545. CF₃ CH₃ H 546. CF₃ H CH₃ 547. OH H H 548. OH CH₃ CH₃ 549. OH CH₃ H 550. OH H CH₃ 551. OH CHO H 552. OH CHO CH₃ 553. OH H CF₃ 554. OH CF₃ H 555. OH CF₃ CF₃ 556. OH CH₂OCH₃ CH₃ 557. OH CH₃ CH₂OCH₃ 558. OH CH₂OCH₃ H 559. OH H CH₂OCH₃ 560. H CHO H 561. CH₃ CHO H 562. CF₃ CHO H 563. CH₂OCH₃ CHO H 564. nBu CHO H 565. H CHO CH₃ 566. CH₃ CHO CH₃ 567. CF₃ CHO CH₃ 568. CH₂OCH₃ CHO CH₃ 569. nBu CHO CH₃ 570. H H CHO 571. CH₃ H CHO 572. CF₃ H CHO 573. CH₂OCH₃ H CHO 574. nBu H CHO 575. H CH₃ CHO 576. CH₃ CH₃ CHO 577. CF₃ CH₃ CHO 578. CH₂OCH₃ CH₃ CHO 579. nBu CH₃ CHO 580. H Cl CH₃ 581. H CH₃ Cl 582. H CF₃ Cl 583. H Cl CF₃ 584. CH₃ Cl CH₃ 585. CH₃ CH₃ Cl 586. CH₃ CF₃ Cl 587. CH₃ Cl CF₃ 588. CF₃ Cl CH₃ 589. CF₃ CH₃ Cl 590. CF₃ CF₃ Cl 591. CF₃ Cl CF₃ 592. OCH₃ H H 593. OCH₃ CH₃ CH₃ 594. OCH₃ CH₃ H 595. OCH₃ H CH₃ 596. OCH₃ CHO H 597. OCH₃ CHO CH₃ 598. OCH₃ H CF₃ 599. OCH₃ CF₃ H 600. OCH₃ CF₃ CF₃ 601. OCH₃ CH₂OCH₃ CH₃ 602. OCH₃ CH₃ CH₂OCH₃ 603. OCH₃ CH₂OCH₃ H 604. OCH₃ H CH₂OCH₃ 605. H Cl OCH₂CH₃ 606. H Cl SCH₂CH₃ 607. H Cl Morpholin 608. H Cl Pyperidin 609. H Pyperidin Pyperidin 610. H

Cl 611. H

Cl 612. H CH₃(CH₂)₁₃O Cl 613. H OCH₂Ph-3-Cl Cl 614. H Cl OCH₂Ph-3-Cl 615. H O(CH₂)₂ CΞCH Cl 616. H OCH(CH₃)═CH₂ Cl 617. H O(CH₂)₂ CH═CH₂ Cl 618. H Cl O(CH₂)₂CH═CH2 619. H

Cl 620. H O(CH₂)₂Ph-4-CN Cl 621. H Cl O(CH₂)₂Ph-4-CN 622. H OCH₂CH₂CH₃ Cl 623. H O(CH₂)₂O(CH₂)₂OCH₃ Cl 624. H CH₃CH₂CH(CH₃)O Cl OCH(CH₃)CH₂CH₃ 625. H OCH₂CH═CH₂ Cl 626. H Cl OCH₂ CH═CH₂ 627. H Cl OCH₂ CΞCH 628. H O(CH₂)₂ CΞCCH₃ Cl 629. H OCH₂ CΞCCH₃ Cl 630. H Cl OCH₂ CΞCCH₃ 631. H OCH(CH₃)-cycloprop. Cl 632. H OCH₂C(CH₃)═CH₂ Cl 633. H Cl OCH₂C(CH₃)═CH₂ 634. H

Cl 635. H Cl

636. H O(CH₂)₂OPh-2-Cl Cl 637. H O—Cl, m-ClPhCH(CH₃)O Cl 638. H O(CH₂)₂SCH₂Ph-4-Cl Cl 639. H O(CH₂)₂Ph-2-Cl Cl 640. H O(CH₂)₂Ph-3-CF₃ Cl 641. H O(CH₂)₂Ph-4-CH₃ Cl 642. H

Cl 643. H

Cl 644. H O (CH₂)₂ CF₃ Cl 645. H

Cl 646. H O (CH₂)₁₁C(O)OCH₃ Cl 647. H

Cl 648. H O(CH₂)₂SCH₃ Cl 649. H O(CH₂)₇CH₃ Cl 650. H OCH₂Ph-3-OCH₃ Cl 651. H

Cl 652. H OC₁₂H₂₄ Cl 653. H O(CH₂)₂O(CH₂)₅CH₃ Cl 654. H O C₁₀H₁₈ Cl 655. H

Cl 656. H O(CH₂)₂SCH₂CH₃ Cl 657. H

Cl 658. H OCH₂CH═CH(CH₂)₂CH₃ Cl 659. H O(CH₂)₂Ph-3,4-(OCH₃)₂ Cl 660. H O(CH₂)₂Ph-4-Cl Cl 661. H CF₃(CF₂)₅CH₂O Cl 662. H

Cl 663. H OCH₂Ph-2-I Cl 664. H CH₃(CH₂)₂O(CH₂)₂O Cl (CH₂)₂O(CH₂)₂O 665. H

Cl 666. H O(CH₂)₃-4-(C₅H₄N) Cl 667. H

Cl 668. H

Cl 669. H O(CH₂)₁₁Br Cl 670. H O(CH₂)₂S Ph Cl 671. H

Cl 672. H

Cl 673. H O(CH₂)₆Ph Cl 674. H

Cl 675. H O(CH₂)₉CH═CH₂ Cl 676. H

Cl 677. H

Cl 678. H OCH₂Ph-3-CF₃ Cl 679. H OCH₂₋3-(C₅H₄N) Cl 680. H OCH₂Si(CH₃)₃ Cl 681. H O(CH₂)₄Cl Cl 682. H

Cl 683. H

Cl 684. H

Cl 685. H SEt SEt 686. H Cl OiPr 687. H Cl NH₂ 688. H Cl N(CH₃)NH₂ 689. H

690. H Cl NHPr 691. H Cl NHPh 692. H Cl NHCH(CH₂)₂ 693. H NHPr Cl 694. H NHCH(CH₂)₂ Cl 695. H Cl NH C₅H₉ 696. H NH C₅H₉ Cl 697. H Cl

698. H Cl N(CH₃)(OCH₃) 699. H Cl NHCH₂CΞCH 700. H Cl NHCH(CH₃)CH₂OCH₃ 701. H Cl NHEt 702. H NHCH₂CΞCH Cl 703. H NHEt Cl 704. H Br Br 705. H iPr Br 706. H OBu Ph 707. H Ph-3,5-(CF₃)₂ Ph-3,5-(CF₃)₂ 708. H Ph-4-CH₃ Ph-4-CH₃ 709. H OiPr Ph 710. H OiPr Ph-4-CH₃ 711. H OiPr Ph-3,5-(CF₃)₂ 712. H OiPr Ph-4- Si (CH₃)₃ 713. H Ph-4-Si (CH₃)₃ Ph-4- Si (CH₃)₃ 714. H OCH₂CΞCH Cl 715. H NHCH₂Ph Cl 716. H Cl NHCH₂Ph 717. H NH₂ Cl 718. H

Cl 719. H

Cl 720. H

Cl 721. H Cl

722. H Cl

723. H OiPr Cl 724. H OEt Cl 725. H NHCH(CH₃)CH₂OCH₃ Cl 726. H SCH₂CH₃ Cl

TABLE B-7 I.7

N^(o) R₃ R₅ R₆ R₇ R₈  1. H H H H H  2. H CH₃ H H H  3. H nBu H H H  4. H CF₃ H H H  5. H CF₂CF₃ H H H  6. H CH₂OCH₃ H H H  7. H OCH₃ H H H  8. H Ph H H H  9. H —CH₂Ph H H H  10. H H H CH₃ H  11. H H H nBu H  12. H H H CF₃ H  13. H H H CF₂CF₃ H  14. H H H CH₂OCH₃ H  15. H H H OCH₃ H  16. H H H Ph H  17. H H H —CH₂Ph H  18. H CH₃ CH₃ H H  19. H nBu CH₃ H H  20. H CF₃ CH₃ H H  21. H CF₂CF₃ CH₃ H H  22. H CH₂OCH₃ CH₃ H H  23. H OCH₃ CH₃ H H  24. H Ph CH₃ H H  25. H —CH₂Ph CH₃ H H  26. H H H CH₃ CH₃  27. H H H CH₃ nBu  28. H H H CH₃ CF₃  29. H H H CH₃ CF₂CF₃  30. H H H CH₃ CH₂OCH₃  31. H H H CH₃ OCH₃  32. H H H CH₃ Ph  33. H H H CH₃ —CH₂Ph  34. H CH₃ H H CH₃  35. H nBu H H CH₃  36. H CF₃ H H CH₃  37. H CF₂CF₃ H H CH₃  38. H CH₂OCH₃ H H CH₃  39. H OCH₃ H H CH₃  40. H Ph H H CH₃  41. H —CH₂Ph H H CH₃  42. H H CH₃ nBu H  43. H H CH₃ CF₃ H  44. H H CH₃ CF₂CF₃ H  45. H H CH₃ CH₂OCH₃ H  46. H H CH₃ OCH₃ H  47. H H CH₃ Ph H  48. H H CH₃ —CH₂Ph H  49. H CH₃ H CH₃ CH₃  50. H nBu H CH₃ CH₃  51. H CF₃ H CH₃ CH₃  52. H CF₂CF₃ H CH₃ CH₃  53. H CH₂OCH₃ H CH₃ CH₃  54. H OCH₃ H CH₃ CH₃  55. H Ph H CH₃ CH₃  56. H —CH₂Ph H CH₃ CH₃  57. H CH₃ CH₃ CH₃ H  58. H CH₃ CH₃ nBu H  59. H CH₃ CH₃ CF₃ H  60. H CH₃ CH₃ CF₂CF₃ H  61. H CH₃ CH₃ CH₂OCH₃ H  62. H CH₃ CH₃ OCH₃ H  63. H CH₃ CH₃ Ph H  64. H CH₃ CH₃ —CH₂Ph H  65. H nBu CH₃ CH₃ H  66. H CF₃ CH₃ CH₃ H  67. H CF₂CF₃ CH₃ CH₃ H  68. H CH₂OCH₃ CH₃ CH₃ H  69. H OCH₃ CH₃ CH₃ H  70. H Ph CH₃ CH₃ H  71. H —CH₂Ph CH₃ CH₃ H  72. H CH₃ H CH₃ nBu  73. H CH₃ H CH₃ CF₃  74. H CH₃ H CH₃ CF₂CF₃  75. H CH₃ H CH₃ CH₂OCH₃  76. H CH₃ H CH₃ OCH₃  77. H CH₃ H CH₃ Ph  78. H CH₃ H CH₃ —CH₂Ph  79. H CH₃ CH₃ CH₃ CH₃  80. H nBu CH₃ CH₃ CH₃  81. H CF₃ CH₃ CH₃ CH₃  82. H CF₂CF₃ CH₃ CH₃ CH₃  83. H CH₂OCH₃ CH₃ CH₃ CH₃  84. H OCH₃ CH₃ CH₃ CH₃  85. H Ph CH₃ CH₃ CH₃  86. H —CH₂Ph CH₃ CH₃ CH₃  87. H CH₃ CH₃ CH₃ nBu  88. H CH₃ CH₃ CH₃ CF₃  89. H CH₃ CH₃ CH₃ CF₂CF₃  90. H CH₃ CH₃ CH₃ CH₂OCH₃  91. H CH₃ CH₃ CH₃ OCH₃  92. H CH₃ CH₃ CH₃ Ph  93. H CH₃ CH₃ CH₃ —CH₂Ph  94. H nBnu nBu H H  95. H CF₃ nBu H H  96. H CF₂CF₃ nBu H H  97. H CH₂OCH₃ nBu H H  98. H OCH₃ nBu H H  99. H Ph nBu H H 100. H —CH₂Ph nBu H H 101. H H H Bu nBu 102. H H H CF₃ nBu 103. H H H CF₂CF₃ nBu 104. H H H CH₂OCH₃ nBu 105. H H H OCH₃ nBu 106. H H H Ph nBu 107. H H H —CH₂Ph nBu 108. H nBu H H H 109. H nBu H H CH₃ 110. H nBu H H nBu 111. H nBu H H CF₃ 112. H nBu H H CF₂CF₃ 113. H nBu H H CH₂OCH₃ 114. H nBu H H OCH₃ 115 H nBu H H Ph 116. H nBu H H —CH₂Ph 117. H H H nBu H 118. H H CH₃ nBu H 119. H H nBu nBu H 120. H H CF₃ nBu H 121. H H CF₂CF₃ nBu H 122. H H CH₂OCH₃ nBu H 123. H H OCH₃ nBu H 124. H H Ph nBu H 125. H H —CH₂Ph nBu H 126. H CH₃ nBu nBu H 127. H nBu nBu nBu H 128. H CF₃ nBu nBu H 129. H CF₂CF₃ nBu nBu H 130. H CH₂OCH₃ nBu nBu H 131. H OCH₃ nBu nBu H 132. H Ph nBu Bu H 133. H —CH₂Ph nBu nBu H 134. H CH₃ H nBu nBu 135. H nBu H nBu nBu 136. H CF₃ H nBu nBu 137. H CF₂CF₃ H nBu nBu 138. H CH₂OCH₃ H nBu nBu 139. H OCH₃ H nBu nBu 140. H Ph H nBu nBu 141. H —CH₂Ph H nBu nBu 142. H nBu nBu CH₃ H 143. H nBu nBu CF₃ H 144. H nBu nBu CF₂CF₃ H 145. H nBu nBu CH₂OCH₃ H 146. H nBu nBu OCH₃ H 147. H nBu nBu Ph H 148. H nBu nBu —CH₂Ph H 149. H nBu H CH₃ nBu 150. H nBu H CF₃ nBu 151. H nBu H CF₂CF₃ nBu 152. H nBu H CH₂OCH₃ nBu 153. H nBu H OCH₃ nBu 154. H nBu H Ph nBu 155. H nBu H —CH₂Ph nBu 156. H CH₃ nBu nBu nBu 157. H Bu nBu nBu nBu 158. H CF₃ nBu nBu nBu 159. H CF₂CF₃ nBu nBu nBu 160. H CH₂OCH₃ nBu nBu nBu 161. H OCH₃ nBu nBu nBu 162. H Ph nBu nBu nBu 163. H —CH₂Ph nBu nBu nBu 164. H nBu nBu nBu CH₃ 165. H nBu nBu nBu CF₃ 166. H nBu nBu nBu CF₂CF₃ 167. H nBu nBu nBu CH₂OCH₃ 168. H nBu nBu nBu OCH₃ 169. H nBu nBu nBu Ph 170. H nBu Bu nBu —CH₂Ph 171. H nBu CH₃ nBu CH₃ 172. H nBu CH₃ nBu CF₃ 173. H nBu CH₃ nBu CF₂CF₃ 174. H nBu CH₃ nBu CH₂OCH₃ 175. H nBu CH₃ nBu OCH₃ 176. H nBu CH₃ nBu Ph 177. H nBu CH₃ nBu —CH₂Ph 178. H CF₃ nBu nBu CH₃ 179. H CF₂CF₃ nBu nBu CH₃ 180. H CH₂OCH₃ nBu nBu CH₃ 181. H OCH₃ nBu nBu CH₃ 182. H Ph nBu nBu CH₃ 183. H —CH₂Ph nBu nBu CH₃ 184. H CH₃ CH₃ nBu nBu 185. H CF₃ CH₃ nBu nBu 186. H CF₂CF₃ CH₃ nBu nBu 187. H CH₂OCH₃ CH₃ nBu nBu 188. H OCH₃ CH₃ nBu nBu 189. H Ph CH₃ nBu nBu 190. H —CH₂Ph CH₃ nBu nBu 191. H nBu nBu CH₃ CH₃ 192. H nBu nBu CF₃ CH₃ 193. H nBu nBu CF₂CF₃ CH₃ 194. H nBu nBu CH₂OCH₃ CH₃ 195. H nBu nBu OCH₃ CH₃ 196. H nBu nBu Ph CH₃ 197. H nBu nBu —CH₂Ph CH₃ 198. H nBu CH₃ CH₃ CF₃ 199. H nBu CH₃ CH₃ CF₂CF₃ 200. H nBu CH₃ CH₃ CH₂OCH₃ 201. H nBu CH₃ CH₃ OCH₃ 202. H nBu CH₃ CH₃ Ph 203. H nBu CH₃ CH₃ —CH₂Ph 204. H CF₃ CH₃ CH₃ nBu 205. H CF₂CF₃ CH₃ CH₃ nBu 206. H CH₂OCH₃ CH₃ CH₃ nBu 207. H OCH₃ CH₃ CH₃ nBu 208. H Ph CH₃ CH₃ nBu 209. H —CH₂Ph CH₃ CH₃ nBu 210. H CF₃ nBu CH₃ CH₃ 211. H CF₂CF₃ nBu CH₃ CH₃ 212. H CH₂OCH₃ nBu CH₃ CH₃ 213. H OCH₃ nBu CH₃ CH₃ 214. H Ph nBu CH₃ CH₃ 215. H —CH₂Ph nBu CH₃ CH₃ 216. H CH₃ CH₃ CF₃ nBu 217. H CH₃ CH₃ CF₂CF₃ nBu 218. H CH₃ CH₃ CH₂OCH₃ nBu 219. H CH₃ CH₃ OCH₃ nBu 220. H CH₃ CH₃ Ph nBu 221. H CH₃ CH₃ —CH₂Ph nBu 222. H CF₃ nBu H CH₃ 223. H CF₂CF₃ nBu H CH₃ 224. H CH₂OCH₃ nBu H CH₃ 225. H OCH₃ nBu H CH₃ 226. H Ph nBu H CH₃ 227. H —CH₂Ph nBu H CH₃ 228. H H CH₃ CF₃ nBu 229. H H CH₃ CF₂CF₃ nBu 230. H H CH₃ CH₂OCH₃ nBu 231. H H CH₃ OCH₃ nBu 232. H H CH₃ Ph nBu 233. H H CH₃ —CH₂Ph nBu 234. H nBu H CH₃ CF₃ 235. H nBu H CH₃ CF₂CF₃ 236. H nBu H CH₃ CH₂OCH₃ 237. H nBu H CH₃ OCH₃ 238. H nBu H CH₃ Ph 239. H nBu H CH₃ —CH₂Ph 240. H CF₃ CH₃ nBu H 241. H CF₂CF₃ CH₃ nBu H 242. H CH₂OCH₃ CH₃ nBu H 243. H OCH₃ CH₃ nBu H 244. H Ph CH₃ nBu H 245. H —CH₂Ph CH₃ nBu H 246. H CF₃ Bu CH₃ H 247. H CF₂CF₃ Bu CH₃ H 248. H CH₂OCH₃ Bu CH₃ H 249. H OCH₃ Bu CH₃ H 250. H Ph Bu CH₃ H 251. H —CH₂Ph Bu CH₃ H 252. H CH₃ H CF₃ nBu 253. H CH₃ H CF₂CF₃ nBu 254. H CH₃ H CH₂OCH₃ nBu 255. H CH₃ H OCH₃ nBu 256. H CH₃ H Ph nBu 257. H CH₃ H —CH₂Ph nBu 258. H nBu CH₃ H CF₃ 259. H nBu CH₃ H CF₂CF₃ 260. H nBu CH₃ H CH₂OCH₃ 261. H nBu CH₃ H OCH₃ 262. H nBu CH₃ H Ph 263. H nBu CH₃ H —CH₂Ph 264. H CF₃ H CH₃ nBu 265. H CF₂CF₃ H CH₃ nBu 266. H CH₂OCH₃ H CH₃ nBu 267. H OCH₃ H CH₃ nBu 268. H Ph H CH₃ nBu 269. H —CH₂Ph H CH₃ nBu 270. CH₃ H H H H 271. CH₃ CH₃ H H H 272. CH₃ nBu H H H 273. CH₃ CF₃ H H H 274. CH₃ CF₂CF₃ H H H 275. CH₃ CH₂OCH₃ H H H 276. CH₃ OCH₃ H H H 277. CH₃ Ph H H H 278. CH₃ —CH₂Ph H H H 279. CH₃ H H CH₃ H 280. CH₃ H H nBu H 281. CH₃ H H CF₃ H 282. CH₃ H H CF₂CF₃ H 283. CH₃ H H CH₂OCH₃ H 284. CH₃ H H OCH₃ H 285. CH₃ H H Ph H 286. CH₃ H H —CH₂Ph H 287. CH₃ CH₃ CH₃ H H 288. CH₃ nBu CH₃ H H 289. CH₃ CF₃ CH₃ H H 290. CH₃ CF₂CF₃ CH₃ H H 291. CH₃ CH₂OCH₃ CH₃ H H 292. CH₃ OCH₃ CH₃ H H 293. CH₃ Ph CH₃ H H 294. CH₃ —CH₂Ph CH₃ H H 295. CH₃ H H CH₃ CH₃ 296. CH₃ H H CH₃ nBu 297. CH₃ H H CH₃ CF₃ 298. CH₃ H H CH₃ CF₂CF₃ 299. CH₃ H H CH₃ CH₂OCH₃ 300. CH₃ H H CH₃ OCH₃ 301. CH₃ H H CH₃ Ph 302. CH₃ H H CH₃ —CH₂Ph 303. CH₃ CH₃ H H CH₃ 304. CH₃ Bu H H CH₃ 305. CH₃ CF₃ H H CH₃ 306. CH₃ CF₂CF₃ H H CH₃ 307. CH₃ CH₂OCH₃ H H CH₃ 308. CH₃ OCH₃ H H CH₃ 309. CH₃ Ph H H CH₃ 310. CH₃ —CH₂Ph H H CH₃ 311. CH₃ H CH₃ nBu H 312. CH₃ H CH₃ CF₃ H 313. CH₃ H CH₃ CF₂CF₃ H 314. CH₃ H CH₃ CH₂OCH₃ H 315. CH₃ H CH₃ OCH₃ H 316. CH₃ H CH₃ Ph H 317. CH₃ H CH₃ —CH₂Ph H 318. CH₃ CH₃ H CH₃ CH₃ 319. CH₃ nBu H CH₃ CH₃ 320. CH₃ CF₃ H CH₃ CH₃ 321. CH₃ CF₂CF₃ H CH₃ CH₃ 322. CH₃ CH₂OCH₃ H CH₃ CH₃ 323. CH₃ OCH₃ H CH₃ CH₃ 324. CH₃ Ph H CH₃ CH₃ 325. CH₃ —CH₂Ph H CH₃ CH₃ 326. CH₃ CH₃ CH₃ CH₃ H 327. CH₃ CH₃ CH₃ nBu H 328. CH₃ CH₃ CH₃ CF₃ H 329. CH₃ CH₃ CH₃ CF₂CF₃ H 330. CH₃ CH₃ CH₃ CH₂OCH₃ H 331. CH₃ CH₃ CH₃ OCH₃ H 332. CH₃ CH₃ CH₃ Ph H 333. CH₃ CH₃ CH₃ —CH₂Ph H 334. CH₃ nBu CH₃ CH₃ H 335. CH₃ CF₃ CH₃ CH₃ H 336. CH₃ CF₂CF₃ CH₃ CH₃ H 337. CH₃ CH₂OCH₃ CH₃ CH₃ H 338. CH₃ OCH₃ CH₃ CH₃ H 339. CH₃ Ph CH₃ CH₃ H 340. CH₃ —CH₂Ph CH₃ CH₃ H 341. CH₃ CH₃ H CH₃ nBu 342. CH₃ CH₃ H CH₃ CF₃ 343. CH₃ CH₃ H CH₃ CF₂CF₃ 344. CH₃ CH₃ H CH₃ CH₂OCH₃ 345. CH₃ CH₃ H CH₃ OCH₃ 346. CH₃ CH₃ H CH₃ Ph 347. CH₃ CH₃ H CH₃ —CH₂Ph 348. CH₃ CH₃ CH₃ CH₃ CH₃ 349. CH₃ nBu CH₃ CH₃ CH₃ 350. CH₃ CF₃ CH₃ CH₃ CH₃ 351. CH₃ CF₂CF₃ CH₃ CH₃ CH₃ 352. CH₃ CH₂OCH₃ CH₃ CH₃ CH₃ 353. CH₃ OCH₃ CH₃ CH₃ CH₃ 354. CH₃ Ph CH₃ CH₃ CH₃ 355. CH₃ —CH₂Ph CH₃ CH₃ CH₃ 356. CH₃ CH₃ CH₃ CH₃ nBu 357. CH₃ CH₃ CH₃ CH₃ CF₃ 358. CH₃ CH₃ CH₃ CH₃ CF₂CF₃ 359. CH₃ CH₃ CH₃ CH₃ CH₂OCH₃ 360. CH₃ CH₃ CH₃ CH₃ OCH₃ 361. CH₃ CH₃ CH₃ CH₃ Ph 362. CH₃ CH₃ CH₃ CH₃ —CH₂Ph 363. CH₃ nBu nBu H H 364. CH₃ CF₃ nBu H H 365. CH₃ CF₂CF₃ nBu H H 366. CH₃ CH₂OCH₃ nBu H H 367. CH₃ OCH₃ nBu H H 368. CH₃ Ph nBu H H 369. CH₃ —CH₂Ph nBu H H 370. CH₃ H H nBu nBu 371. CH₃ H H CF₃ nBu 372. CH₃ H H CF₂CF₃ nBu 373. CH₃ H H CH₂OCH₃ nBu 374. CH₃ H H OCH₃ nBu 375. CH₃ H H Ph nBu 376. CH₃ H H —CH₂Ph nBu 377. CH₃ nBu H H H 378. CH₃ nBu H H CH₃ 379. CH₃ nBu H H nBu 380. CH₃ nBu H H CF₃ 381. CH₃ nBu H H CF₂CF₃ 382. CH₃ nBu H H CH₂OCH₃ 383. CH₃ nBu H H OCH₃ 384. CH₃ nBu H H Ph 385. CH₃ nBu H H —CH₂Ph 386. CH₃ H H nBu H 387. CH₃ H CH₃ nBu H 388. CH₃ H Bu nBu H 389. CH₃ H CF₃ nBu H 390. CH₃ H CF₂CF₃ nBu H 391. CH₃ H CH₂OCH₃ nBu H 392. CH₃ H OCH₃ nBu H 393. CH₃ H Ph nBu H 394. CH₃ H —CH₂Ph nBu H 395. CH₃ CH₃ nBu nBu H 396. CH₃ nBu nBu nBu H 397. CH₃ CF₃ nBu nBu H 398. CH₃ CF₂CF₃ nBu nBu H 399. CH₃ CH₂OCH₃ nBu nBu H 400. CH₃ OCH₃ nBu nBu H 401. CH₃ Ph nBu nBu H 402. CH₃ —CH₂Ph nBu nBu H 403. CH₃ CH₃ H nBu nBu 404. CH₃ nBu H nBu nBu 405. CH₃ CF₃ H nBu nBu 406. CH₃ CF₂CF₃ H nBu nBu 407. CH₃ CH₂OCH₃ H nBu nBu 408. CH₃ OCH₃ H nBu nBu 409. CH₃ Ph H nBu nBu 410. CH₃ —CH₂Ph H nBu nBu 411. CH₃ nBu nBu CH₃ H 412. CH₃ nBu nBu CF₃ H 413. CH₃ nBu nBu CF₂CF₃ H 414. CH₃ nBu nBu CH₂OCH₃ H 415. CH₃ nBu nBu OCH₃ H 416. CH₃ nBu nBu Ph H 417. CH₃ nBu nBu —CH₂Ph H 418. CH₃ nBu H CH₃ nBu 419. CH₃ nBu H CF₃ nBu 420. CH₃ nBu H CF₂CF₃ nBu 421. CH₃ nBu H CH₂OCH₃ nBu 422. CH₃ nBu H OCH₃ nBu 423. CH₃ nBu H Ph nBu 424. CH₃ nBu H —CH₂Ph nBu 425. CH₃ CH₃ nBu nBu nBu 426. CH₃ Bu nBu nBu nBu 427. CH₃ CF₃ nBu nBu nBu 428. CH₃ CF₂CF₃ nBu nBu nBu 429. CH₃ CH₂OCH₃ nBu nBu nBu 430. CH₃ OCH₃ nBu nBu nBu 431. CH₃ Ph nBu nBu nBu 432. CH₃ —CH₂Ph nBu nBu nBu 433. CH₃ nBu nBu nBu CH₃ 434. CH₃ nBu nBu nBu CF₃ 435. CH₃ nBu nBu nBu CF₂CF₃ 436. CH₃ nBu nBu nBu CH₂OCH₃ 437. CH₃ nBu nBu nBu OCH₃ 438. CH₃ nBu nBu nBu Ph 439. CH₃ nBu nBu nBu —CH₂Ph 440. CH₃ nBu CH₃ nBu CH₃ 441. CH₃ nBu CH₃ nBu CF₃ 442. CH₃ nBu CH₃ nBu CF₂CF₃ 443. CH₃ nBu CH₃ nBu CH₂OCH₃ 444. CH₃ nBu CH₃ nBu OCH₃ 445. CH₃ nBu CH₃ nBu Ph 446. CH₃ nBu CH₃ nBu —CH₂Ph 447. CH₃ CF₃ nBu nBu CH₃ 448. CH₃ CF₂CF₃ nBu nBu CH₃ 449. CH₃ CH₂OCH₃ nBu nBu CH₃ 450. CH₃ OCH₃ nBu nBu CH₃ 451. CH₃ Ph nBu nBu CH₃ 452. CH₃ —CH₂Ph nBu nBu CH₃ 453. CH₃ CH₃ CH₃ nBu nBu 454. CH₃ CF₃ CH₃ nBu nBu 455. CH₃ CF₂CF₃ CH₃ nBu nBu 456. CH₃ CH₂OCH₃ CH₃ nBu nBu 457. CH₃ OCH₃ CH₃ nBu nBu 458. CH₃ Ph CH₃ nBu nBu 459. CH₃ —CH₂Ph CH₃ nBu nBu 460. CH₃ nBu nBu CH₃ CH₃ 461. CH₃ nBu nBu CF₃ CH₃ 462. CH₃ nBu nBu CF₂CF₃ CH₃ 463. CH₃ nBu nBu CH₂OCH₃ CH₃ 464. CH₃ nBu nBu OCH₃ CH₃ 465. CH₃ nBu nBu Ph CH₃ 466. CH₃ nBu nBu —CH₂Ph CH₃ 467. CH₃ nBu CH₃ CH₃ CF₃ 468. CH₃ nBu CH₃ CH₃ CF₂CF₃ 469. CH₃ nBu CH₃ CH₃ CH₂OCH₃ 470. CH₃ nBu CH₃ CH₃ OCH₃ 471. CH₃ nBu CH₃ CH₃ Ph 472. CH₃ nBu CH₃ CH₃ —CH₂Ph 473. CH₃ CF₃ CH₃ CH₃ nBu 474. CH₃ CF₂CF₃ CH₃ CH₃ nBu 475. CH₃ CH₂OCH₃ CH₃ CH₃ nBu 476. CH₃ OCH₃ CH₃ CH₃ nBu 477. CH₃ Ph CH₃ CH₃ nBu 478. CH₃ —CH₂Ph CH₃ CH₃ nBu 479. CH₃ CF₃ nBu CH₃ CH₃ 480. CH₃ CF₂CF₃ nBu CH₃ CH₃ 481. CH₃ CH₂OCH₃ nBu CH₃ CH₃ 482. CH₃ OCH₃ nBu CH₃ CH₃ 483. CH₃ Ph nBu CH₃ CH₃ 484. CH₃ —CH₂Ph nBu CH₃ CH₃ 485. CH₃ CH₃ CH₃ CF₃ nBu 486. CH₃ CH₃ CH₃ CF₂CF₃ nBu 487. CH₃ CH₃ CH₃ CH₂OCH₃ nBu 488. CH₃ CH₃ CH₃ OCH₃ nBu 489. CH₃ CH₃ CH₃ Ph nBu 490. CH₃ CH₃ CH₃ —CH₂Ph nBu 491. CH₃ CF₃ nBu H CH₃ 492. CH₃ CF₂CF₃ nBu H CH₃ 493. CH₃ CH₂OCH₃ nBu H CH₃ 494. CH₃ OCH₃ nBu H CH₃ 495. CH₃ Ph nBu H CH₃ 496. CH₃ —CH₂Ph nBu H CH₃ 497. CH₃ H CH₃ CF₃ nBu 498. CH₃ H CH₃ CF₂CF₃ nBu 499. CH₃ H CH₃ CH₂OCH₃ nBu 500. CH₃ H CH₃ OCH₃ nBu 501. CH₃ H CH₃ Ph nBu 502. CH₃ H CH₃ —CH₂Ph nBu 503. CH₃ nBu H CH₃ CF₃ 504. CH₃ nBu H CH₃ CF₂CF₃ 505. CH₃ nBu H CH₃ CH₂OCH₃ 506. CH₃ nBu H CH₃ OCH₃ 507. CH₃ nBu H CH₃ Ph 508. CH₃ nBu H CH₃ —CH₂Ph 509. CH₃ CF₃ CH₃ nBu H 510. CH₃ CF₂CF₃ CH₃ nBu H 511. CH₃ CH₂OCH₃ CH₃ nBu H 512. CH₃ OCH₃ CH₃ nBu H 513. CH₃ Ph CH₃ nBu H 514. CH₃ —CH₂Ph CH₃ nBu H 515. CH₃ CF₃ nBu CH₃ H 516. CH₃ CF₂CF₃ nBu CH₃ H 517. CH₃ CH₂OCH₃ nBu CH₃ H 518. CH₃ OCH₃ nBu CH₃ H 519. CH₃ Ph nBu CH₃ H 520. CH₃ —CH₂Ph nBu CH₃ H 521. CH₃ CH₃ H CF₃ nBu 522. CH₃ CH₃ H CF₂CF₃ nBu 523. CH₃ CH₃ H CH₂OCH₃ nBu 524. CH₃ CH₃ H OCH₃ nBu 525. CH₃ CH₃ H Ph nBu 526. CH₃ CH₃ H —CH₂Ph nBu 527. CH₃ nBu CH₃ H CF₃ 528. CH₃ nBu CH₃ H CF₂CF₃ 529. CH₃ nBu CH₃ H CH₂OCH₃ 530. CH₃ nBu CH₃ H OCH₃ 531. CH₃ nBu CH₃ H Ph 532. CH₃ nBu CH₃ H —CH₂Ph 533. CH₃ CF₃ H CH₃ nBu 534. CH₃ CF₂CF₃ H CH₃ nBu 535. CH₃ CH₂OCH₃ H CH₃ nBu 536. CH₃ OCH₃ H CH₃ nBu 537. CH₃ Ph H CH₃ nBu 538. CH₃ —CH₂Ph H CH₃ nBu 539. CF₃ H H H H 540. CF₃ CH₃ H H H 541. CF₃ nBu H H H 542. CF₃ CF₃ H H H 543. CF₃ CF₂CF₃ H H H 544. CF₃ CH₂OCH₃ H H H 545. CF₃ OCH₃ H H H 546. CF₃ Ph H H H 547. CF₃ —CH₂Ph H H H 548. CF₃ H H CH₃ H 549. CF₃ H H nBu H 550. CF₃ H H CF₃ H 551. CF₃ H H CF₂CF₃ H 552. CF₃ H H CH₂OCH₃ H 553. CF₃ H H OCH₃ H 554. CF₃ H H Ph H 555. CF₃ H H —CH₂Ph H 556. CF₃ CH₃ CH₃ H H 557. CF₃ nBu CH₃ H H 558. CF₃ CF₃ CH₃ H H 559. CF₃ CF₂CF₃ CH₃ H H 560. CF₃ CH₂OCH₃ CH₃ H H 561. CF₃ OCH₃ CH₃ H H 562. CF₃ Ph CH₃ H H 563. CF₃ —CH₂Ph CH₃ H H 564. CF₃ H H CH₃ CH₃ 565. CF₃ H H CH₃ nBu 566. CF₃ H H CH₃ CF₃ 567. CF₃ H H CH₃ CF₂CF₃ 568. CF₃ H H CH₃ CH₂OCH₃ 569. CF₃ H H CH₃ OCH₃ 570. CF₃ H H CH₃ Ph 571. CF₃ H H CH₃ —CH₂Ph 572. CF₃ CH₃ H H CH₃ 573. CF₃ nBu H H CH₃ 574. CF₃ CF₃ H H CH₃ 575. CF₃ CF₂CF₃ H H CH₃ 576. CF₃ CH₂OCH₃ H H CH₃ 577. CF₃ OCH₃ H H CH₃ 578. CF₃ Ph H H CH₃ 579. CF₃ —CH₂Ph H H CH₃ 580. CF₃ H CH₃ nBu H 581. CF₃ H CH₃ CF₃ H 582. CF₃ H CH₃ CF₂CF₃ H 583. CF₃ H CH₃ CH₂OCH₃ H 584. CF₃ H CH₃ OCH₃ H 585. CF₃ H CH₃ Ph H 586. CF₃ H CH₃ —CH₂Ph H 587. CF₃ CH₃ H CH₃ CH₃ 588. CF₃ nBu H CH₃ CH₃ 589. CF₃ CF₃ H CH₃ CH₃ 590. CF₃ CF₂CF₃ H CH₃ CH₃ 591. CF₃ CH₂OCH₃ H CH₃ CH₃ 592. CF₃ OCH₃ H CH₃ CH₃ 593. CF₃ Ph H CH₃ CH₃ 594. CF₃ —CH₂Ph H CH₃ CH₃ 595. CF₃ CH₃ CH₃ CH₃ H 596. CF₃ CH₃ CH₃ nBu H 597. CF₃ CH₃ CH₃ CF₃ H 598. CF₃ CH₃ CH₃ CF₂CF₃ H 599. CF₃ CH₃ CH₃ CH₂OCH₃ H 600. CF₃ CH₃ CH₃ OCH₃ H 601. CF₃ CH₃ CH₃ Ph H 602. CF₃ CH₃ CH₃ —CH₂Ph H 603. CF₃ nBu CH₃ CH₃ H 604. CF₃ CF₃ CH₃ CH₃ H 605. CF₃ CF₂CF₃ CH₃ CH₃ H 606. CF₃ CH₂OCH₃ CH₃ CH₃ H 607. CF₃ OCH₃ CH₃ CH₃ H 608. CF₃ Ph CH₃ CH₃ H 609. CF₃ —CH₂Ph CH₃ CH₃ H 610. CF₃ CH₃ H CH₃ nBu 611. CF₃ CH₃ H CH₃ CF₃ 612. CF₃ CH₃ H CH₃ CF₂CF₃ 613. CF₃ CH₃ H CH₃ CH₂OCH₃ 614. CF₃ CH₃ H CH₃ OCH₃ 615. CF₃ CH₃ H CH₃ Ph 616. CF₃ CH₃ H CH₃ —CH₂Ph 617. CF₃ CH₃ CH₃ CH₃ CH₃ 618. CF₃ nBu CH₃ CH₃ CH₃ 619. CF₃ CF₃ CH₃ CH₃ CH₃ 620. CF₃ CF₂CF₃ CH₃ CH₃ CH₃ 621. CF₃ CH₂OCH₃ CH₃ CH₃ CH₃ 622. CF₃ OCH₃ CH₃ CH₃ CH₃ 623. CF₃ Ph CH₃ CH₃ CH₃ 624. CF₃ —CH₂Ph CH₃ CH₃ CH₃ 625. CF₃ CH₃ CH₃ CH₃ nBu 626. CF₃ CH₃ CH₃ CH₃ CF₃ 627. CF₃ CH₃ CH₃ CH₃ CF₂CF₃ 628. CF₃ CH₃ CH₃ CH₃ CH₂OCH₃ 629. CF₃ CH₃ CH₃ CH₃ OCH₃ 630. CF₃ CH₃ CH₃ CH₃ Ph 631. CF₃ CH₃ CH₃ CH₃ —CH₂Ph 632. CF₃ Bu nBu H H 633. CF₃ CF₃ nBu H H 634. CF₃ CF₂CF₃ nBu H H 635. CF₃ CH₂OCH₃ nBu H H 636. CF₃ OCH₃ nBu H H 637. CF₃ Ph nBu H H 638. CF₃ —CH₂Ph nBu H H 639. CF₃ H H nBu nBu 640. CF₃ H H CF₃ nBu 641. CF₃ H H CF₂CF₃ nBu 642. CF₃ H H CH₂OCH₃ nBu 643. CF₃ H H OCH₃ nBu 644. CF₃ H H Ph nBu 645. CF₃ H H —CH₂Ph nBu 646. CF₃ nBu H H H 647. CF₃ nBu H H CH₃ 648. CF₃ nBu H H Bu 649. CF₃ nBu H H CF₃ 650. CF₃ nBu H H CF₂CF₃ 651. CF₃ nBu H H CH₂OCH₃ 652. CF₃ nBu H H OCH₃ 653. CF₃ nBu H H Ph 654. CF₃ nBu H H —CH₂Ph 655. CF₃ H H nBu H 656. CF₃ H CH₃ nBu H 657. CF₃ H Bu nBu H 658. CF₃ H CF₃ nBu H 659. CF₃ H CF₂CF₃ nBu H 660. CF₃ H CH₂OCH₃ nBu H 661. CF₃ H OCH₃ nBu H 662. CF₃ H Ph nBu H 663. CF₃ H —CH₂Ph nBu H 664. CF₃ CH₃ nBu nBu H 665. CF₃ Bu nBu nBu H 666. CF₃ CF₃ nBu nBu H 667. CF₃ CF₂CF₃ nBu nBu H 668. CF₃ CH₂OCH₃ nBu nBu H 669. CF₃ OCH₃ nBu nBu H 670. CF₃ Ph nBu nBu H 671. CF₃ —CH₂Ph nBu nBu H 672. CF₃ CH₃ H nBu nBu 673. CF₃ nBu H nBu nBu 674. CF₃ CF₃ H nBu nBu 675. CF₃ CF₂CF₃ H nBu nBu 676. CF₃ CH₂OCH₃ H nBu nBu 677. CF₃ OCH₃ H nBu nBu 678. CF₃ Ph H nBu nBu 679. CF₃ —CH₂Ph H nBu nBu 680. CF₃ nBu nBu CH₃ H 681. CF₃ nBu nBu CF₃ H 682. CF₃ nBu nBu CF₂CF₃ H 683. CF₃ nBu nBu CH₂OCH₃ H 684. CF₃ nBu nBu OCH₃ H 685. CF₃ nBu nBu Ph H 686. CF₃ nBu nBu —CH₂Ph H 687. CF₃ nBu H CH₃ nBu 688. CF₃ nBu H CF₃ nBu 689. CF₃ nBu H CF₂CF₃ nBu 690. CF₃ nBu H CH₂OCH₃ nBu 691. CF₃ nBu H OCH₃ nBu 692. CF₃ nBu H Ph nBu 693. CF₃ nBu H —CH₂Ph nBu 694. CF₃ CH₃ nBu nBu nBu 695. CF₃ nBu nBu nBu nBu 696. CF₃ CF₃ nBu nBu nBu 697. CF₃ CF₂CF₃ nBu nBu nBu 698. CF₃ CH₂OCH₃ nBu nBu nBu 699. CF₃ OCH₃ nBu nBu nBu 700. CF₃ Ph nBu nBu nBu 701. CF₃ —CH₂Ph nBu nBu nBu 702. CF₃ nBu nBu nBu CH₃ 703. CF₃ nBu nBu nBu CF₃ 704. CF₃ nBu nBu nBu CF₂CF₃ 705. CF₃ nBu nBu nBu CH₂OCH₃ 706. CF₃ nBu nBu nBu OCH₃ 707. CF₃ nBu nBu nBu Ph 708. CF₃ nBu nBu nBu —CH₂Ph 709. CF₃ nBu CH₃ nBu CH₃ 710. CF₃ nBu CH₃ nBu CF₃ 711. CF₃ nBu CH₃ nBu CF₂CF₃ 712. CF₃ nBu CH₃ nBu CH₂OCH₃ 713. CF₃ nBu CH₃ nBu OCH₃ 714. CF₃ nBu CH₃ nBu Ph 715. CF₃ nBu CH₃ nBu —CH₂Ph 716. CF₃ CF₃ nBu nBu CH₃ 717. CF₃ CF₂CF₃ nBu nBu CH₃ 718. CF₃ CH₂OCH₃ nBu nBu CH₃ 719. CF₃ OCH₃ nBu nBu CH₃ 720. CF₃ Ph nBu nBu CH₃ 721. CF₃ —CH₂Ph nBu nBu CH₃ 722. CF₃ CH₃ CH₃ nBu nBu 723. CF₃ CF₃ CH₃ nBu nBu 724. CF₃ CF₂CH₃ CH₃ nBu nBu 725. CF₃ CH₂OCH₃ CH₃ nBu nBu 726. CF₃ OCH₃ CH₃ nBu nBu 727. CF₃ Ph CH₃ nBu nBu 728. CF₃ —CH₂Ph CH₃ nBu nBu 729. CF₃ nBu nBu CH₃ CH₃ 730. CF₃ nBu nBu CF₃ CH₃ 731. CF₃ nBu nBu CF₂CF₃ CH₃ 732. CF₃ nBu nBu CH₂OCH₃ CH₃ 733. CF₃ nBu nBu OCH₃ CH₃ 734. CF₃ nBu nBu Ph CH₃ 735. CF₃ nBu nBu —CH₂Ph CH₃ 736. CF₃ nBu CH₃ CH₃ CF₃ 737. CF₃ nBu CH₃ CH₃ CF₂CF₃ 738. CF₃ nBu CH₃ CH₃ CH₂OCH₃ 739. CF₃ nBu CH₃ CH₃ OCH₃ 740. CF₃ nBu CH₃ CH₃ Ph 741. CF₃ nBu CH₃ CH₃ —CH₂Ph 742. CF₃ CF₃ CH₃ CH₃ nBu 743. CF₃ CF₂CF₃ CH₃ CH₃ nBu 744. CF₃ CH₂OCH₃ CH₃ CH₃ nBu 745. CF₃ OCH₃ CH₃ CH₃ nBu 746. CF₃ Ph CH₃ CH₃ nBu 747. CF₃ —CH₂Ph CH₃ CH₃ nBu 748. CF₃ CF₃ nBu CH₃ CH₃ 749. CF₃ CF₂CF₃ nBu CH₃ CH₃ 750. CF₃ CH₂OCH₃ nBu CH₃ CH₃ 751. CF₃ OCH₃ nBu CH₃ CH₃ 752. CF₃ Ph nBu CH₃ CH₃ 753. CF₃ —CH₂Ph nBu CH₃ CH₃ 754. CF₃ CH₃ CH₃ CF₃ nBu 755. CF₃ CH₃ CH₃ CF₂CF₃ nBu 756. CF₃ CH₃ CH₃ CH₂OCH₃ nBu 757. CF₃ CH₃ CH₃ OCH₃ nBu 758. CF₃ CH₃ CH₃ Ph nBu 759. CF₃ CH₃ CH₃ —CH₂Ph nBu 760. CF₃ CF₃ nBu H CH₃ 761. CF₃ CF₂CF₃ nBu H CH₃ 762. CF₃ CH₂OCH₃ nBu H CH₃ 763. CF₃ OCH₃ nBu H CH₃ 764. CF₃ Ph nBu H CH₃ 765. CF₃ —CH₂Ph nBu H CH₃ 766. CF₃ H CH₃ CF₃ nBu 767. CF₃ H CH₃ CF₂CF₃ nBu 768. CF₃ H CH₃ CH₂OCH₃ nBu 769. CF₃ H CH₃ OCH₃ nBu 770. CF₃ H CH₃ Ph nBu 771. CF₃ H CH₃ —CH₂Ph nBu 772. CF₃ nBu H CH₃ CF₃ 773. CF₃ nBu H CH₃ CF₂CF₃ 774. CF₃ nBu H CH₃ CH₂OCH₃ 775. CF₃ nBu H CH₃ OCH₃ 776. CF₃ nBu H CH₃ Ph 777. CF₃ nBu H CH₃ —CH₂Ph 778. CF₃ CF₃ CH₃ nBu H 779. CF₃ CF₂CF₃ CH₃ nBu H 780. CF₃ CH₂OCH₃ CH₃ nBu H 781. CF₃ OCH₃ CH₃ nBu H 782. CF₃ Ph CH₃ nBu H 783. CF₃ —CH₂Ph CH₃ nBu H 784. CF₃ CF₃ nBu CH₃ H 785. CF₃ CF₂CF₃ nBu CH₃ H 786. CF₃ CH₂OCH₃ nBu CH₃ H 787. CF₃ OCH₃ nBu CH₃ H 788. CF₃ Ph nBu CH₃ H 789. CF₃ —CH₂Ph nBu CH₃ H 790. CF₃ CH₃ H CF₃ nBu 791. CF₃ CH₃ H CF₂CF₃ nBu 792. CF₃ CH₃ H CH₂OCH₃ nBu 793. CF₃ CH₃ H OCH₃ nBu 794. CF₃ CH₃ H Ph nBu 795. CF₃ CH₃ H —CH₂Ph nBu 796. CF₃ nBu CH₃ H CF₃ 797. CF₃ nBu CH₃ H CF₂CF₃ 798. CF₃ nBu CH₃ H CH₂OCH₃ 799. CF₃ nBu CH₃ H OCH₃ 800. CF₃ nBu CH₃ H Ph 801. CF₃ nBu CH₃ H —CH₂Ph 802. CF₃ CF₃ H CH₃ nBu 803. CF₃ CF₂CF₃ H CH₃ nBu 804. CF₃ CH₂OCH₃ H CH₃ nBu 805. CF₃ OCH₃ H CH₃ nBu 806. CF₃ Ph H CH₃ nBu 807. CF₃ —CH₂Ph H CH₃ nBu 808. Ph H H H H 809. Ph CH₃ H H H 810. Ph H H CH₃ H 811. Ph CH₃ CH₃ H H 812. Ph H H CH₃ CH₃ 813. Ph CF₃ H H H 814. Ph H H CF₃ H 815. OH H H H H 816. OH CH₃ H H H 817. OH H H CH₃ H 818. OH CH₃ CH₃ H H 819. OH H H CH₃ CH₃ 820. OH H H CF₃ H 821. OH CF₃ H H CH₃ 822. OH CF₃ H H H 823. OH CH₃ H CF₃ H 824. OH H H CH₂OCH₃ H 825. OH CH₂OCH₃ H H H 826. OH CH₂OCH₃ H CH₃ H 827. OH H CH₃ CH₂OCH₃ H 828. OH CH₂OCH₃ H CH₃ H 829. OH H CH₃ CH₂OCH₃ H 830. CH₃ H (CH₂)₄ H

TABLE B-8

R₅ R₆ R₇ R₈ R₉ 1. H H H H H 2. CH₃ H H H H 3. n-Bu H H H H 4. CF₃ H H H H 5. CF₂CF₃ H H H H 6. CH₂OCH₃ H H H H 7. OCH₃ H H H H 8. Ph H H H H 9. —CH₂Ph H H H H 10. H H CH₃ H H 11. H H n-Bu H H 12. H H CF H H 13. H H CF₂CF₃ H H 14. H H CH₂OCH₃ H H 15. H H OCH₃ H H 16. H H Ph H H 17. H H —CH₂Ph H H 18. CH₃ CH₃ H H H 19. n-Bu CH₃ H H H 20. CF₃ CH₃ H H H 21. CF₂CF₃ CH₃ H H H 22. CH₂OCH₃ CH₃ H H H 23. OCH₃ CH₃ H H H 24. Ph CH₃ H H H 25. —CH₂Ph CH₃ H H H 26. H H CH₃ CH₃ H 27. H H CH₃ n-Bu H 28. H H CH₃ CF₃ H 29. H H CH₃ CF₂CF₃ H 30. H H CH₃ CH₂OCH₃ H 31. H H CH₃ OCH₃ H 32. H H CH₃ Ph H 33. H H CH₃ CH₂Ph H 34. CH₃ H H CH₃ H 35. n-Bu H H CH₃ H 36. CF₃ H H CH₃ H 37. CF₂CF₃ H H CH₃ H 38. CH₂OCH₃ H H CH₃ H 39. OCH₃ H H CH₃ H 40. Ph H H CH₃ H 41. —CH₂Ph H H CH₃ H 42. H CH₃ n-Bu H H 43. H CH₃ CF₃ H H 44. H CH₃ CF₂CF₃ H H 45. H CH₃ CH₂OCH₃ H H 46. H CH₃ OCH₃ H H 47. H CH₃ Ph H H 48. H CH₃ —CH₂Ph H H 49. CH₃ H CH₃ CH₃ H 50. n-Bu H CH₃ CH₃ H 51. CF₃ H CH₃ CH₃ H 52. CF₂CF₃ H CH₃ CH₃ H 53. CH₂OCH₃ H CH₃ CH₃ H 54. OCH₃ H CH₃ CH₃ H 55. Ph H CH₃ CH₃ H 56. CH₂Ph H CH₃ CH₃ H 57. CH₃ CH₃ CH₃ H H 58. CH₃ CH₃ n-Bu H H 59. CH₃ CH₃ CF₃ H H 60. CH₃ CH₃ CF₂CF₃ H H 61. CH₃ CH₃ CH₂OCH₃ H H 62. CH₃ CH₃ CH₃ H H 63. CH₃ CH₃ Ph H H 64. CH₃ CH₃ —CH₂Ph H H 65. n-Bu CH₃ CH₃ H H 66. CF₃ CH₃ CH₃ H H 67. CF₂CF₃ CH₃ CH₃ H H 68. CH₂OCH₃ CH₃ CH₃ H H 69. OCH₃ CH₃ CH₃ H H 70. Ph CH₃ CH₃ H H 71. CH₂Ph CH₃ CH₃ H H 72. CH₃ H CH₃ n-Bu H 73. CH₃ H CH₃ CF₃ H 74. CH₃ H CH₃ CF₂CF₃ H 75. CH₃ H CH₃ CH₂OCH₃ H 76. CH₃ H CH₃ CH₃ H 77. CH₃ H CH₃ Ph H 78. CH₃ H CH₃ CH₂Ph H 79. CH₃ CH₃ CH₃ CH₃ H 80. n-Bu CH₃ CH₃ CH₃ H 81. CF₃ CH₃ CH₃ CH₃ H 82. CF₂CF₃ CH₃ CH₃ CH₃ H 83. CH₂OCH₃ CH₃ CH₃ CH₃ H 84. CH₃ CH₃ CH₃ CH₃ H 85. Ph CH₃ CH₃ CH₃ H 86. CH₂Ph CH₃ CH₃ CH₃ H 87. CH₃ CH₃ CH₃ n-Bu H 88. CH₃ CH₃ CH₃ CF₃ H 89. CH₃ CH₃ CH₃ CF₂CF₃ H 90. CH₃ CH₃ CH₃ CH₂CH₃ H 91. CH₃ CH₃ CH₃ CH₃ H 92. CH₃ CH₃ CH₃ Ph H 93. CH₃ CH₃ CH₃ CH₂Ph H 94. n-Bu n-Bu H H H 95. CF₃ n-Bu H H H 96. CF₂CF₃ n-Bu H H H 97. CH₂OCH₃ n-Bu H H H 98. OCH₃ n-Bu H H H 99. Ph n-Bu H H H 100. CH₂Ph n-Bu H H H 101. H H n-Bu n-Bu H 102. H H CF₃ n-Bu H 103. H H CF₂CF₃ n-Bu H 104. H H CH₂OCH₃ n-Bu H 105. H H OCH₃ n-Bu H 106. H H Ph n-Bu H 107. H H —CH₂Ph n-Bu H 108. n-Bu H H H H 109. n-Bu H H CH₃ H 110. n-Bu H H v H 111. n-Bu H H CF₃ H 112. n-Bu H H CF₂CF₃ H 113. n-Bu H H CH₂OCH₃ H 114. n-Bu H H OCH₃ H 115. n-Bu H H Ph H 116. n-Bu H H —CH₂Ph H 117. H H n-Bu H H 118. H CH₃ n-Bu H H 119. H n-Bu n-Bu H H 120. H CF₃ n-Bu H H 121. H CF₂CF₃ n-Bu H H 122. H CH₂OCH₃ n-Bu H H 123. H OCH₃ n-Bu H H 124. H Ph n-Bu H H 125. H -CH₂Ph n-Bu H H 126. CH₃ n-Bu n-Bu H H 127. n-Bu n-Bu n-Bu H H 128. CF₃ n-Bu n-Bu H H 129. CF₂CF₃ n-Bu n-Bu H H 130. CH₂OCH₃ n-Bu n-Bu H H 131. OCH₃ n-Bu n-Bu H H 132. Ph n-Bu n-Bu H H 133. —CH₂Ph n-Bu n-Bu H H 134. CH₃ H n-Bu n-Bu H 135. n-Bu H n-Bu n-Bu H 136. CF₃ H n-Bu n-Bu H 137. CF₂CF₃ H n-Bu n-Bu H 138. CH₂OCH₃ H n-Bu n-Bu H 139. OCH₃ H n-Bu n-Bu H 140. Ph H n-Bu n-Bu H 141. —CH₂Ph H n-Bu n-Bu H 142. n-Bu n-Bu CH₃ H H 143. n-Bu n-Bu CF₃ H H 144. n-Bu n-Bu CF₂CF₃ H H 145. n-Bu n-Bu CH₂OCH₃ H H 146. n-Bu n-Bu OCH₃ H H 147. n-Bu n-Bu Ph H H 148. n-Bu n-Bu —CH₂Ph H H 149. n-Bu H CH₃ n-Bu H 150. n-Bu H CF₃ n-Bu H 151. n-Bu H CF₂CF₃ n-Bu H 152. n-Bu H CH₂OCH₃ n-Bu H 153. n-Bu H OCH₃ n-Bu H 154. n-Bu H Ph n-Bu H 155. n-Bu H —CH₂Ph n-Bu H 156. CH3 n-Bu n-Bu n-Bu H 157. n-Bu n-Bu n-Bu n-Bu H 158. CF3 n-Bu n-Bu n-Bu H 159. CF₂CF₃ n-Bu n-Bu n-Bu H 160. CH₂OCH₃ n-Bu n-Bu n-Bu H 161. OCH₃ n-Bu n-Bu n-Bu H 162. Ph n-Bu n-Bu n-Bu H 163. —CH₂Ph n-Bu n-Bu n-Bu H 164. n-Bu n-Bu n-Bu CH₃ H 165. n-Bu n-Bu n-Bu CF3 H 166. n-Bu n-Bu n-Bu CF₂CF₃ H 167. n-Bu n-Bu n-Bu CH₂OCH₃ H 168. n-Bu n-Bu n-Bu OCH₃ H 169. n-Bu n-Bu n-Bu Ph H 170. n-Bu n-Bu n-Bu —CH₂Ph H 171. n-Bu CH₃ n-Bu CH₃ H 172. n-Bu CH₃ n-Bu CF₃ H 173. n-Bu CH₃ n-Bu CF₂CF₃ H 174. n-Bu CH₃ n-Bu CH₂OCH₃ H 175. n-Bu CH₃ n-Bu OCH₃ H 176. n-Bu CH₃ n-Bu Ph H 177. n-Bu CH₃ n-Bu —CH₂Ph H 178. CF₃ n-Bu n-Bu CH₃ H 179. CF₂CF₃ n-Bu n-Bu CH₃ H 180. CH₂OCH₃ n-Bu n-Bu CH₃ H 181. OCH₃ n-Bu n-Bu CH₃ H 182. Ph n-Bu n-Bu CH₃ H 183. —CH₂Ph n-Bu n-Bu CH₃ H 184. CH₃ CH₃ n-Bu n-Bu H 185. CF₃ CH₃ n-Bu n H 186. CF₂CF₃ CH₃ n-Bu n H 187. CH₂OCH₃ CH₃ n-Bu n H 188. OCH₃ CH₃ n-Bu n H 189. Ph CH₃ n-Bu n H 190. —CH₂Ph CH₃ n-Bu n H 191. n-Bu n-Bu CH₃ CH₃ H 192. n-Bu n-Bu CF₃ CH₃ H 193. n-Bu n-Bu CF₂CF₃ CH₃ H 194. n-Bu n-Bu CH₂OCH₃ CH₃ H 195. n-Bu n-Bu OCH₃ CH₃ H 196. n-Bu n-Bu Ph CH₃ H 197. n-Bu n-Bu —CH₂Ph CH₃ H 198. n-Bu CH₃ CH₃ CF₃ H 199. n-Bu CH₃ CH₃ CF₂CF₃ H 200. n-Bu CH₃ CH₃ CH₂OCH₃ H 201. n-Bu CH₃ CH₃ OCH₃ H 202. n-Bu CH₃ CH₃ Ph H 203. n-Bu CH₃ CH₃ —CH₂Ph H 204. CF₃ CH₃ CH₃ n-Bu H 205. CF₂CF₃ CH₃ CH₃ n-Bu H 206. CH₂OCH₃ CH₃ CH₃ n-Bu H 207. OCH₃ CH₃ CH₃ n-Bu H 208. Ph CH₃ CH₃ n-Bu H 209. —CH₂Ph CH₃ CH₃ n-Bu H 210. CF₃ n-Bu CH₃ CH₃ H 211. CF₂CF₃ n-Bu CH₃ CH₃ H 212. CH₂OCH₃ n-Bu CH₃ CH₃ H 213. OCH₃ n-Bu CH₃ CH₃ H 214. Ph n-Bu CH₃ CH₃ H 215. —CH₂Ph n-Bu CH₃ CH₃ H 216. CH₃ CH₃ CF₃ n-Bu H 217. CH₃ CH₃ CF₂CF₃ n-Bu H 218. CH₃ CH₃ CH₂OCH₃ n-Bu H 219. CH₃ CH₃ OCH₃ n-Bu H 220. CH₃ CH₃ Ph n-Bu H 221. CH₃ CH₃ —CH₂Ph n-Bu H 222. CF₃ n-Bu H CH₃ H 223. CF₂CF₃ n-Bu H CH₃ H 224. CH₂OCH₃ n-Bu H CH₃ H 225. OCH₃ n-Bu H CH₃ H 226. Ph n-Bu H CH₃ H 227. —CH₂Ph n-Bu H CH₃ H 228. H CH₃ CF₃ n-Bu H 229. H CH₃ CF₂CF₃ n-Bu H 230. H CH₃ CH₂OCH₃ n-Bu H 231. H CH₃ OCH₃ n-Bu H 232. H CH₃ Ph n-Bu H 233. H CH₃ —CH₂Ph n-Bu H 234. n-Bu H CH₃ CF₃ H 235. n-Bu H CH₃ CF₂CF₃ H 236. n-Bu H CH₃ CH₂OCH₃ H 237. n-Bu H CH₃ OCH₃ H 238. n-Bu H CH₃ Ph H 239. n-Bu H CH₃ —CH₂Ph H 240. CF₃ CH₃ n-Bu H H 241. CF₂CF₃ CH₃ n-Bu H H 242. CH₂OCH₃ CH₃ n-Bu H H 243. OCH₃ CH₃ n-Bu H H 244. Ph CH₃ n-Bu H H 245. —CH₂Ph CH₃ n-Bu H H 246. CF₃ n-Bu CH₃ H H 247. CF₂CF₃ n-Bu CH₃ H H 248. CH₂OCH₃ n-Bu CH₃ H H 249. OCH₃ n-Bu CH₃ H H 250. Ph n-Bu CH₃ H H 251. —CH₂Ph n-Bu CH₃ H H 252. CH₃ H CF₃ n-Bu H 253. CH₃ H CF₂CF₃ n-Bu H 254. CH₃ H CH₂OCH₃ n-Bu H 255. CH₃ H OCH₃ n-Bu H 256. CH₃ H Ph n-Bu H 257. CH₃ H —CH₂Ph n-Bu H 258. n-Bu CH₃ H CF₃ H 259. n-Bu CH₃ H CF₂CF₃ H 260. n-Bu CH₃ H CH₂OCH₃ H 261. n-Bu CH₃ H OCH₃ H 262. n-Bu CH₃ H Ph H 263. n-Bu CH₃ H —CH₂Ph H 264. CF₃ H CH₃ n-Bu H 265. CF₂CF₃ H CH₃ n-Bu H 266. CH₂OCH₃ H CH₃ n-Bu H 267. OCH₃ H CH₃ n-Bu H 268. Ph H CH₃ n-Bu H 269. —CH₂Ph H CH₃ n-Bu H 270. H H H H CH₃ 271. CH₃ H H H CH₃ 272. n-Bu H H H CH₃ 273. CF₃ H H H CH₃ 274. CF₂CF₃ H H H CH₃ 275. CH₂OCH₃ H H H CH₃ 276. OCH₃ H H H CH₃ 277. Ph H H H CH₃ 278. —CH₂Ph H H H CH₃ 279. H H CH₃ H CH₃ 280. H H n-Bu H CH₃ 281. H H CF₃ H CH₃ 282. H H CF₂CF₃ H CH₃ 283. H H CH₂OCH₃ H CH₃ 284. H H OCH₃ H CH₃ 285. H H Ph H CH₃ 286. H H —CH₂Ph H CH₃ 287. CH₃ CH₃ H H CH₃ 288. n-Bu CH₃ H H CH₃ 289. CF₃ CH₃ H H CH₃ 290. CF₂CF₃ CH₃ H H CH₃ 291. CH₂OCH₃ CH₃ H H CH₃ 292. OCH₃ CH₃ H H CH₃ 293. Ph CH₃ H H CH₃ 294. —CH₂Ph CH₃ H H CH₃ 295. H H CH₃ CH₃ CH₃ 296. H H CH₃ n-Bu CH₃ 297. H H CH₃ CF₃ CH₃ 298. H H CH₃ CF₂CF₃ CH₃ 299. H H CH₃ CH₂OCH₃ CH₃ 300. H H CH₃ OCH₃ CH₃ 301. H H CH₃ Ph CH₃ 302. H H CH₃ —CH₂Ph CH₃ 303. CH₃ H H CH₃ CH₃ 304. n-Bu H H CH₃ CH₃ 305. CF₃ H H CH₃ CH₃ 306. CF₂CF₃ H H CH₃ CH₃ 307. CH₂OCH₃ H H CH₃ CH₃ 308. OCH₃ H H CH₃ CH₃ 309. Ph H H CH₃ CH₃ 310. —CH₂Ph H H CH₃ CH₃ 311. H CH₃ n-Bu H CH₃ 312. H CH₃ CF₃ H CH₃ 313. H CH₃ CF₂CF₃ H CH₃ 314. H CH₃ CH₂OCH₃ H CH₃ 315. H CH₃ OCH₃ H CH₃ 316. H CH₃ Ph H CH₃ 317. H CH₃ —CH₂Ph H CH₃ 318. CH₃ H CH₃ CH₃ CH₃ 319. n-Bu H CH₃ CH₃ CH₃ 320. CF₃ H CH₃ CH₃ CH₃ 321. CF₂CF₃ H CH₃ CH₃ CH₃ 322. CH₂OCH₃ H CH₃ CH₃ CH₃ 323. OCH₃ H CH₃ CH₃ CH₃ 324. Ph H CH₃ CH₃ CH₃ 325. —CH₂Ph H CH₃ CH₃ CH₃ 326. CH₃ CH₃ CH₃ H CH₃ 327. CH₃ CH₃ n-Bu H CH₃ 328. CH₃ CH₃ CF₃ H CH₃ 329. CH₃ CH₃ CF₂CF₃ H CH₃ 330. CH₃ CH₃ CH2CH₃ H CH₃ 331. CH₃ CH₃ OCH₃ H CH₃ 332. CH₃ CH₃ Ph H CH₃ 333. CH₃ CH₃ —CH₂Ph H CH₃ 334. n-Bu CH₃ CH₃ H CH₃ 335. CF₃ CH₃ CH₃ H CH₃ 336. CF₂CF₃ CH₃ CH₃ H CH₃ 337. CH₂OCH₃ CH₃ CH₃ H CH₃ 338. OCH₃ CH₃ CH₃ H CH₃ 339. Ph CH₃ CH₃ H CH₃ 340. —CH₂Ph CH₃ CH₃ H CH₃ 341. CH₃ H CH₃ n-Bu CH₃ 342. CH₃ H CH₃ CF₃ CH₃ 343. CH₃ H CH₃ CF₂CF₃ CH₃ 344. CH₃ H CH₃ CH₂OCH₃ CH₃ 345. CH₃ H CH₃ OCH₃ CH₃ 346. CH₃ H CH₃ Ph CH₃ 347. CH₃ H CH₃ —CH₂Ph CH₃ 348. CH₃ CH₃ CH₃ CH₃ CH₃ 349. n-Bu CH₃ CH₃ CH₃ CH₃ 350. CF₃ CH₃ CH₃ CH₃ CH₃ 351. CF₂CF₃ CH₃ CH₃ CH₃ CH₃ 352. CH₂OCH₃ CH₃ CH₃ CH₃ CH₃ 353. OCH₃ CH₃ CH₃ CH₃ CH₃ 354. Ph CH₃ CH₃ CH₃ CH₃ 355. —CH₂Ph CH₃ CH₃ CH₃ CH₃ 356. CH₃ CH₃ CH₃ n-Bu CH₃ 357. CH₃ CH₃ CH₃ CF₃ CH₃ 358. CH₃ CH₃ CH₃ CF₂CF₃ CH₃ 359. CH₃ CH₃ CH₃ CH₂OCH₃ CH₃ 360. CH₃ CH₃ CH₃ OCH₃ CH₃ 361. CH₃ CH₃ CH₃ Ph CH₃ 362. CH₃ CH₃ CH₃ —CH₂Ph CH₃ 363. n-Bu n-Bu H H CH₃ 364. CF₃ n-Bu H H CH₃ 365. CF₂CF₃ n-Bu H H CH₃ 366. CH₂OCH₃ n-Bu H H CH₃ 367. OCH₃ n-Bu H H CH₃ 368. Ph n-Bu H H CH₃ 369. —CH₂Ph n-Bu H H CH₃ 370. H H n-Bu n-Bu CH₃ 371. H H CF₃ n-Bu CH₃ 372. H H CF₂CF₃ n-Bu CH₃ 373. H H CH₂OCH₃ n-Bu CH₃ 374. H H OCH₃ n-Bu CH₃ 375. H H Ph n-Bu CH₃ 376. H H —CH₂Ph n-Bu CH₃ 377. n-Bu H H H CH₃ 378. n-Bu H H CH₃ CH₃ 379. n-Bu H H n-Bu CH₃ 380. n-Bu H H CF₃ CH₃ 381. n-Bu H H CF₂CF₃ CH₃ 382. n-Bu H H CH₂OCH₃ CH₃ 383. n-Bu H H OCH₃ CH₃ 384. n-Bu H H Ph CH₃ 385. n-Bu H H —CH₂Ph CH₃ 386. H H n-Bu H CH₃ 387. H CH₃ n-Bu H CH₃ 388. H n-Bu n-Bu H CH₃ 389. H CF₃ n-Bu H CH₃ 390. H CF₂CF₃ n-Bu H CH₃ 391. H CH₂OCH₃ n-Bu H CH₃ 392. H OCH₃ n-Bu H CH₃ 393. H Ph n-Bu H CH₃ 394. H —CH₂Ph n-Bu H CH₃ 395. CH₃ n-Bu n-Bu H CH₃ 396. n-Bu n-Bu n-Bu H CH₃ 397. CF₃ n-Bu n-Bu H CH₃ 398. CF₂CF₃ n-Bu n-Bu H CH₃ 399. CH₂OCH₃ n-Bu n-Bu H CH₃ 400. OCH₃ n-Bu n-Bu H CH₃ 401. Ph n-Bu n-Bu H CH₃ 402. —CH₂Ph n-Bu n-Bu H CH₃ 403. CH₃ H n-Bu n-Bu CH₃ 404. n-Bu H n-Bu n-Bu CH₃ 405. CF₃ H n-Bu n-Bu CH₃ 406. CF₂CF₃ H n-Bu n-Bu CH₃ 407. CH₂OCH₃ H n-Bu n-Bu CH₃ 408. OCH₃ H n-Bu n-Bu CH₃ 409. Ph H n-Bu n-Bu CH₃ 410. —CH₂Ph H n-Bu n-Bu CH₃ 411. n-Bu n-Bu CH₃ H CH₃ 412. n-Bu n-Bu CF₃ H CH₃ 413. n-Bu n-Bu CF₂CF₃ H CH₃ 414. n-Bu n-Bu CH₂OCH₃ H CH₃ 415. n-Bu n-Bu OCH₃ H CH₃ 416. n-Bu n-Bu Ph H CH₃ 417. n-Bu n-Bu —CH₂Ph H CH₃ 418. n-Bu H CH₃ n-Bu CH₃ 419. n-Bu H CF₃ n-Bu CH₃ 420. n-Bu H CF₂CF₃ n-Bu CH₃ 421. n-Bu H CH₂OCH₃ n-Bu CH₃ 422. n-Bu H OCH₃ n-Bu CH₃ 423. n-Bu H Ph n-Bu CH₃ 424. n-Bu H —CH₂Ph n-Bu CH₃ 425. CH₃ n-Bu n-Bu n-Bu CH₃ 426. n-Bu n-Bu n-Bu n-Bu CH₃ 427. CF₃ n-Bu n-Bu n-Bu CH₃ 428. CF₂CF₃ n-Bu n-Bu n-Bu CH₃ 429. CH₂OCH₃ n-Bu n-Bu n-Bu CH₃ 430. OCH₃ n-Bu n-Bu n-Bu CH₃ 431. Ph n-Bu n-Bu n-Bu CH₃ 432. —CH₂Ph n-Bu n-Bu n-Bu CH₃ 433. n-Bu n-Bu n-Bu CH₃ CH₃ 434. n-Bu n-Bu n-Bu CF₃ CH₃ 435. n-Bu n-Bu n-Bu CF₂CF₃ CH₃ 436. n-Bu n-Bu n-Bu CH₂OCH₃ CH₃ 437. n-Bu n-Bu n-Bu OCH₃ CH₃ 438. n-Bu n-Bu n-Bu Ph CH₃ 439. n-Bu n-Bu n-Bu —CH₂Ph CH₃ 440. n-Bu CH₃ n-Bu CH₃ CH₃ 441. n-Bu CH₃ n-Bu CF₃ CH₃ 442. n-Bu CH₃ n-Bu CF₂CF₃ CH₃ 443. n-Bu CH₃ n-Bu CH₂OCH₃ CH₃ 444. n-Bu CH₃ n-Bu OCH₃ CH₃ 445. n-Bu CH₃ n-Bu Ph CH₃ 446. n-Bu CH₃ n-Bu —CH₂Ph CH₃ 447. CF₃ n-Bu n-Bu CH₃ CH₃ 448. CF₂CF₃ n-Bu n-Bu CH₃ CH₃ 449. CH₂OCH₃ n-Bu n-Bu CH₃ CH₃ 450. OCH₃ n-Bu n-Bu CH₃ CH₃ 451. Ph n-Bu n-Bu CH₃ CH₃ 452. —CH₂Ph n-Bu n-Bu CH₃ CH₃ 453. CH₃ CH₃ n-Bu n-Bu CH₃ 454. CF₃ CH₃ n-Bu n-Bu CH₃ 455. CF₂CF₃ CH₃ n-Bu n-Bu CH₃ 456. CH₂OCH₃ CH₃ n-Bu n-Bu CH₃ 457. OCH₃ CH₃ n-Bu n-Bu CH₃ 458. Ph CH₃ n-Bu n-Bu CH₃ 459. —CH₂Ph CH₃ n-Bu n-Bu CH₃ 460. n-Bu n-Bu CH₃ CH₃ CH₃ 461. n-Bu n-Bu CF₃ CH₃ CH₃ 462. n-Bu n-Bu CF₂CF₃ CH₃ CH₃ 463. n-Bu n-Bu CH₂OCH₃ CH₃ CH₃ 464. n-Bu n-Bu OCH₃ CH₃ CH₃ 465. n-Bu n-Bu Ph CH₃ CH₃ 466. n-Bu n-Bu —CH₂Ph CH₃ CH₃ 467. n-Bu CH₃ CH₃ CF₃ CH₃ 468. n-Bu CH₃ CH₃ CF₂CF₃ CH₃ 469. n-Bu CH₃ CH₃ CH₂OCH₃ CH₃ 470. n-Bu CH₃ CH₃ OCH₃ CH₃ 471. n-Bu CH₃ CH₃ Ph CH₃ 472. n-Bu CH₃ CH₃ —CH₂Ph CH₃ 473. CF₃ CH₃ CH₃ n-Bu CH₃ 474. CF₂CF₃ CH₃ CH₃ n-Bu CH₃ 475. CH₂OCH₃ CH₃ CH₃ n-Bu CH₃ 476. CH₃ CH₃ CH₃ n-Bu CH₃ 477. Ph CH₃ CH₃ n-Bu CH₃ 478. —CH₂Ph CH₃ CH₃ n-Bu CH₃ 479. CF₃ n-Bu CH₃ CH₃ CH₃ 480. CF₂CF₃ n-Bu CH₃ CH₃ CH₃ 481. CH₂OCH₃ n-Bu CH₃ CH₃ CH₃ 482. OCH₃ n-Bu CH₃ CH₃ CH₃ 483. Ph n-Bu CH₃ CH₃ CH₃ 484. —CH₂Ph n-Bu CH₃ CH₃ CH₃ 485. CH₃ CH₃ CF₃ n-Bu CH₃ 486. CH₃ CH₃ CF₂CF₃ n-Bu CH₃ 487. CH₃ CH₃ CH₂OCH₃ n-Bu CH₃ 488. CH₃ CH₃ OCH₃ n-Bu CH₃ 489. CH₃ CH₃ Ph n-Bu CH₃ 490. CH₃ CH₃ —CH₂Ph n-Bu CH₃ 491. CF₃ n-Bu H CH₃ CH₃ 492. CF₂CF₃ n-Bu H CH₃ CH₃ 493. CH₂OCH₃ n-Bu H CH₃ CH₃ 494. OCH₃ n-Bu H CH₃ CH₃ 495. Ph n-Bu H CH₃ CH₃ 496. —CH₂Ph n-Bu H CH₃ CH₃ 497. H CH₃ CF₃ n-Bu CH₃ 498. H CH₃ CF₂CF₃ n-Bu CH₃ 499. H CH₃ CH₂OCH₃ n-Bu CH₃ 500. H CH₃ OCH₃ n-Bu CH₃ 501. H CH₃ Ph n-Bu CH₃ 502. H CH₃ —CH₂Ph n-Bu CH₃ 503. n-Bu H CH₃ CF₃ CH₃ 504. n-Bu H CH₃ CF₂CF₃ CH₃ 505. n-Bu H CH₃ CH₂OCH₃ CH₃ 506. n-Bu H CH₃ OCH₃ CH₃ 507. n-Bu H CH₃ Ph CH₃ 508. n-Bu H CH₃ —CH₂Ph CH₃ 509. CF₃ CH₃ n-Bu H CH₃ 510. CF₂CF₃ CH₃ n-Bu H CH₃ 511. CH₂OCH₃ CH₃ n-Bu H CH₃ 512. OCH₃ CH₃ n-Bu H CH₃ 513. Ph CH₃ n-Bu H CH₃ 514. —CH₂Ph CH₃ n-Bu H CH₃ 515. CF₃ n-Bu CH₃ H CH₃ 516. CF₂CF₃ n-Bu CH₃ H CH₃ 517. CH₂OCH₃ n-Bu CH₃ H CH₃ 518. OCH₃ n-Bu CH₃ H CH₃ 519. Ph n-Bu CH₃ H CH₃ 520. —CH₂Ph n-Bu CH₃ H CH₃ 521. CH₃ H CF₃ n-Bu CH₃ 522. CH₃ H CF₂CF₃ n-Bu CH₃ 523. CH₃ H CH₂OCH₃ n-Bu CH₃ 524. CH₃ H OCH₃ n-Bu CH₃ 525. CH₃ H Ph n-Bu CH₃ 526. CH₃ H —CH₂Ph n-Bu CH₃ 527. n-Bu CH₃ H CF₃ CH₃ 528. n-Bu CH₃ H CF₂CF₃ CH₃ 529. n-Bu CH₃ H CH₂OCH₃ CH₃ 530. n-Bu CH₃ H OCH₃ CH₃ 531. n-Bu CH₃ H Ph CH₃ 532. n-Bu CH₃ H —CH₂Ph CH₃ 533. CF₃ H CH₃ n-Bu CH₃ 534. CF₂CF₃ H CH₃ n-Bu CH₃ 535. CH₂OCH₃ H CH₃ n-Bu CH₃ 536. OCH₃ H CH₃ n-Bu CH₃ 537. Ph H CH₃ n-Bu CH₃ 538. —CH₂Ph H CH₃ n-Bu CH₃ 539. H —CH₂— H CH₃ 540. H —(CH₂)₄— H CH₃

For the following example compounds physico-chemical data have been obtained and are displayed in order to illustrate the working of the present invention, including the outlined methods of synthesis. The number of given data may not be interpreted as a limitation of the invention. Analysis of compounds 6.610 to 6.684: Reversed-phase was performed on a Waters Alliance 2790 LC equiped with a Waters996 UV detector using a YMC CombiScreen ODS-AQ cartridge (30×4.6 mm, S-5 □m, 12 um) Mobile phase: A: H₂O/CH₃CN 10/TFA, B: CH₃CN/TFA 0.1, C: MeOH.Gradient: 89% A 11% B, 0-3.5 min; 90% B 10% C 0.5 min. TABLE C Comp. No. from Table B Table A Melting point [° C.] or ¹H-NMR [δ in ppm] 1.001 028 122-131 1.002 028 199-201 1.003 028 (DMSO); 0.60(t, 3H), 1.19(s, 3H), 1.67(q, 2H), 2.02(s, 3H), 6.93(dd, 1H), 7.26(t, 1H), 7.47(d, 1H), 7.76(dd, 1H), 7.83(dd, 1H), 7.93(dd, 1H), 8.48(d, 1H), 8.55(d, 1H), 8.63(d, 1H), 10.00(s, NH); 1.004 028 187-192 1.005 028 (CDCl₃); 1.80(s, 3H), 2.14(s, 3H), 7.00(dd, 1H), 7.22-7.29(m, 7H), 7.39(dd, 1H), 7.72(s, 1H), 7.84(s, 1H), 8.52(d, 1H), 8.70(dd, 1H), 8.77(s, NH); 1.006 028 167-168 1.007 028  90-92 1.008 028  95-99 1.009 028 (DMSO); 1.41(s, 3H), 2.18(s, 3H), 3.10(s, 2H), 7.04(d, 1H), 7.14(s, 5H), 7.38(t, 1H), 7.50(d, 1H), 7.85(d, 1H), 7.92(d, 1H), 7.98(s, 1H), 8.42(s, 1H), 8.55(d, 1H), 8.71(d, 1H), 10.09(s, NH); 1.010 028 165-168 1.011 028 215-219 1.012 028 210 1.050 028 202-205 1.051 028 164-167 1.052 028 167-170 1.053 028 189-192 2.002 028 181-185 2.003 028 204-208 2.004 028 210 2.005 028 190-192 2.006 028 199-203 2.007 028 180-182 2.008 048 127-135 2.009 028  87-83 2.010 028 195-197 2.011 028 187-189 2.012 028 218-220 3.001 028 163-166 3.002 028 189-191 3.003 028 158 3.011 028 (DMSO); 3.32(s, 3H), 4.35(s, 2H), 5.66(s, 1H), 7.03(dd, 1H), 7.35(t, 1H), 7.62(m, 1H), 7.77(m, 1H), 8.00(m, 1H), 8.20(m, 1H), 8.48(m, 1H), 8.62(d, 1H), 8.74(d, 1H), 10.12(s, NH), 12.25(s, 1H); 3.012 028 158-159 3.013 028 167 3.014 028 141-150 3.015 028 (DMSO); 1.74(s, 3H), 2.15(s, 3H), 7.01(dd, 1H), 7.37(t, 1H), 7.46(s, 1H), 7.82(s, 1H), 7.93(d, 2H), 8.55(d, 1H), 8.63(d, 1H), 9.21(s, 1H), 10.07(s, NH), 11.5/12.0(s, 1H); 3.016 028 (DMSO); 1.85(s, 3H), 7.02(dd, 1H), 7.35-7.79(m, 7H), 8.61(d, 1H), 8.74(d, 1H), 10.12(s, NH), 11.7/11.9(s, 1H); 3.017 028 185-188 3.018 028 171-174 3.019 028 149-150 3.020 028 155-157 3.027 028 178-180 3.028 028 181-184 3.029 028 199-201 3.030 028 120-125 3.031 028 169-170 3.032 028 184 3.033 028 171-175 3.034 028 163-167 3.035 028 152-161 3.036 028 115-119 3.037 028 182-185 3.038 028 160-163 3.039 028 210 3.040 028 184 3.041 028 210 5.001 028 143-144 5.002 028 151-153 5.003 028 166-168 5.004 028 200-202 1.001 048 (DMSO); 1.31(s, 6H), 2.14(s, 3H), 3.42(s, 3H), 5.49(s, 2H), 7.37-7.60(m, 5H), 7.88(dd, 1H), 8.54(s, 1H), 8.61(d, 1H), 8.64(d, 1H); 6.002 028 238-240 6.003 028 120-125 6.012 028 229-231 6.015 028 173-175 6.020 028 184-186 6.152 028 213-215 6.153 028 118-127 6.177 028 184-186 6.179 028 187-189 6.605 028 196-198 6.606 028  79-84 6.607 028 153-156 6.608 028 110-120 6.609 028 213-216 6.610 028 RT 3.3 MS 614.2(Area MS 100%, AreaUV 100%) 6.611 028 RT 3.23 MS 564.2 (Area MS100%, AreaUV 100%) 6.612 028 RT 3.9 MS 622.3(Area MS 100%, AreaUV 100%) 6.613 028 RT 2.37 MS 550(Area MS 100%, AreaUV 100%) 6.614 028 RT 2.37 MS 550(Area MS 100%, AreaUV 100%) 6.615 048 RT 2.15 MS 478.1(Area MS 100%, AreaUV 100%) 6.616 028 RT 2.4 MS 480.1(Area MS 100%, AreaUV 84%) 6.617 028 RT 2.37 MS 480.1(Area MS 100%, AreaUV 100%) 6.618 028 RT 2.1 MS 480.1(Area MS 100%, AreaUV 88%) 6.619 028 RT 2.32 MS 480.1(Area MS 100%, AreaUV 100%) 6.620 028 RT 2.1 MS 555.1 (Area MS 100%, AreaUV 90%) 6.621 028 RT 2.1 MS 555.1 (Area MS 100%, AreaUV 90%) 6.622 028 RT 2.1 MS 468.1(Area MS 100%, AreaUV 85%) 6.623 028 RT 1.54 MS 572.1(Area MS 100%, AreaUV 89%) 6.624 028 RT 2.5 MS 482.1(Area MS 100%, AreaUV 100%) 6.625 028 RT 2.24 MS 466.1(Area MS 100%, AreaUV 100%) 6.626 028 RT 1.95 MS 466.1(Area MS 100%, AreaUV 100%) 6.627 028 RT 1.85 MS 464.1(Area MS 100%, AreaUV 100%) 6.628 028 RT 2.1 MS 492.1(Area MS 100%, AreaUV 92%) 6.629 028 RT 2 MS 478.1(Area MS 100%, AreaUV 100%) 6.630 028 RT 2 MS 478.1(Area MS 100%, AreaUV 100%) 6.631 028 RT 2.5 MS 494.1(Area MS 100%, AreaUV 93%) 6.632 028 RT 2.1 MS 480.1(Area MS 100%, AreaUV 74%) 6.633 028 RT 2.1 MS 480.1(Area MS 100%, AreaUV 74%) 6.634 028 RT 2.24 MS 494.1(Area MS 100%, AreaUV 100%) 6.635 028 RT 2.24 MS 494.1(Area MS 100%, AreaUV 100%) 6.636 028 RT 3.1; 3.2 MS 580.1(Area MS 70%, AreaUV 62%) 6.637 028 RT 4 MS 598(Area MS 77%, AreaUV 100%) 6.638 028 RT 3.47 MS 610.1(Area MS 58%, AreaUV 100%) 6.639 028 RT 3.5 MS 564.1(Area MS 67%, AreaUV 100%) 6.640 028 RT 3.4 MS 598.1(Area MS 79%, AreaUV 80%) 6.641 028 RT 3.22 MS 560.1(Area MS 69%, AreaUV 100%) 6.642 028 RT 3.07 MS 660.1(Area MS 100%, AreaUV 100%) 6.643 028 RT 3.1 MS 514(Area MS 59%, AreaUV 100%) 6.644 028 RT 2.8 MS 522.1(Area MS 72%, AreaUV 100%) 6.645 028 RT 3.07 MS 548(Area MS 80%, AreaUV 100%) 6.646 028 RT 4.4 MS 638.2(Area MS 90%, AreaUV 62%) 6.647 028 RT 3.5 MS 580.1(Area MS 57%, AreaUV 100%) 6.648 028 RT 2.81; 2.8 MS 500.1(Area MS 63%, AreaUV 100%) 6.649 028 RT 4 MS 538.2(Area MS 84%, AreaUV 100%) 6.650 028 RT 3.11 MS 546.1(Area MS 53%, AreaUV 80%) 6.651 028 RT 2.7; 2.8 MS 540.1(Area MS 56%, AreaUV 74%) 6.652 028 RT 4.5 MS 592.2(Area MS 62%, AreaUV 100%) 6.653 028 RT 3.5 MS 554.2(Area MS 96%, AreaUV 100%) 6.654 028 RT 4.3 MS 562.2(Area MS 71%, AreaUV 100%) 6.655 028 RT 3.47 MS 494.1(Area MS 100%, AreaUV 100%) 6.656 028 RT 3 MS 514.1(Area MS 86%, AreaUV 100%) 6.657 028 RT 2.2 MS 551.1(Area MS 74%, AreaUV 100%) 6.658 028 RT 3.36 MS 508.1(Area MS 100%, AreaUV 100%) 6.659 028 RT 3.22 MS 590.1(Area MS 84%, AreaUV 100%) 6.660 028 RT 3.3 MS 564.1(Area MS 69%, AreaUV 74%) 6.661 028 RT 3.8 MS 758(Area MS 42%, AreaUV 100%) 6.662 028 RT 3.4 MS 566.1(Area MS 78%, AreaUV 100%) 6.663 028 RT 3.4 MS 642(Area MS 80%, AreaUV 100%) 6.664 028 RT 3 MS 614.2(Area MS 82%, AreaUV 100%) 6.665 028 RT 2.4 MS 512.1(Area MS 92%, AreaUV 82%) 6.666 028 RT 2.0; 2.3 MS 545.1(Area MS 82%, AreaUV 100%) 6.667 028 RT 3.2 MS 494.1(Area MS 74%, AreaUV 100%) 6.668 028 RT 3.4 MS 596.1(Area MS 75%, AreaUV 100%) 6.669 028 RT 4.4 MS 658.1(Area MS 66%, AreaUV 100%) 6.670 028 RT 3.3 MS 562.1(Area MS 81%, AreaUV 100%) 6.671 028 RT 3.1 MS 585(Area MS 70%, AreaUV 100%) 6.672 028 RT 2.04; 2.1 MS 531.1(Area MS 84%, AreaUV 100%) 6.673 028 RT 3.9 MS 586.2(Area MS 88%, AreaUV 100%) 6.674 028 RT 3 MS 522(Area MS 91%, AreaUV 100%) 6.675 028 RT 4.3 MS 578.2(Area MS 88%, AreaUV 100%) 6.676 028 RT 2.78; 2.8 MS 512.1(Area MS 100%, AreaUV 100%) 6.677 028 RT 2.7 MS 525.1(Area MS 95%, AreaUV 100%) 6.678 028 RT 3.3 MS 584.1(Area MS 91%, AreaUV 100%) 6.679 028 RT 1.8; 2.1 MS 517.1(Area MS 72%, AreaUV 100%) 6.680 028 RT 3.7 MS 512.1(Area MS 96%, AreaUV 100%) 6.681 028 RT 3 MS 516.1(Area MS 54%, AreaUV 38%) 6.682 028 RT 3.5 MS 708(Area MS 71%, AreaUV 100%) 6.683 028 RT 3.7 MS 720.1(Area MS 81%, AreaUV 100%) 6.684 028 RT 3.1 MS 607.1(Area MS 88%, AreaUV 100%) 6.685 028  80-100 6.686 028 183-186 6.687 028 212-215 6.688 028 176-178 6.689 028 183-185 6.690 028 110-115 6.691 028 119-123 6.692 028 117-120 6.693 028  83-89 6.694 028  90-100 6.695 028  73-76 6.696 028 110-120 6.697 028 145-160 6.698 028  84-90 6.699 028 239-242 6.700 028  90-105 6.701 028 232-235 6.702 028 178-182 6.703 028 142-148 6.704 028 222-225 6.705 028  75-85 6.706 028 142-144 6.707 028 235-240 6.708 028 141-144 6.709 028  80-82 6.710 028  82-84 6.711 028 174-176 6.712 028 201-203 6.713 028 120-125 6.714 028 198-200 RT 2.06 MS 464.1(Area MS 100%, AreaUV 100%) 6.715 028  85-90 6.716 028  87-97 6.717 028 251-253 6.718 028 RT 2.41 MS 512.1 (Area MS 100%, AreaUV 0%) 6.719 028 RT 2.63 MS 510.1(Area MS 88%, AreaUV 100%) 6.720 028 RT 2.4 MS 482.1(Area MS 90%, AreaUV 82%) 6.721 028  92-96 6.722 028  90-100 6.723 028 110-115 6.724 028 188-190 6.725 028  70-80 6.726 028 182-184 7.001 028 110-130 7.270 028 189-192 7.271 028 207-209 7.277 028  89-93 7.303 028 177-179 7.808 028 165-167 7.830 028  90-95 8.270 028 201-204 8.271 028 193-195 8.277 028 105-115 8.279 028  95-100 8.285 028  98-105 8.303 028 105-110 8.539 028  80-85 8.540 028  95-100

In the following, examples of test systems in plant protection are provided which can demonstrate the efficiency of the compounds of the formula I (designated as “active ingredient” or “test compounds”):

Biological Examples Example B-1 Effect Against Puccinia graminis on Wheat (Brownrust on Wheat)

a) Residual Protective Activity

1 week old wheat plants cv. Arina are treated with the formulated test-compound (0.02% active substance) in a spray chamber. Two days after application wheat plants are inoculated by spraying a spore suspension (1×10⁵ ureidospores/ml) on the test plants. After an incubation period of 1 day at +20° C. and 95% relative atmospheric humidity (r. h.) plants are kept for 9 days at +20° C. and 60% r.h. in a greenhouse. The disease incidence is assessed 10 days after inoculation. At the indicated concentration compounds 1.01/028; 2.02/028; 1.03/028; 1.07/028; 2.03/028; 2.05/028; 2.06/028 exhibited over 70% control of the fungal infection in this test.

Example B-2 Effect Against Phytophthora infestans on Tomatoes (Late Blight on Potato)

a) Residual Protective Activity

3 week old tomato plants cv. Roter Gnom are treated with the formulated test compound (0.02% active substance) in a spray chamber. Two day after application the plants are inoculated by spraying a sporangia suspension (2×10⁴ sporangia/ml) on the test plants. After an incubation period of 4 days at +18° C. and 95% r. h. in a growth chamber the disease incidence is assessed.

At the indicated concentration compounds 1.01/028; 1.03/028; 1.04/028; 1.07/028 exhibited over 70% control of the fungal infection in this test.

Example B-3 Effect Against Phytophthora infestans/Potato (Late Blight on Potato)

5 week old potato plants cv. Bintje are treated with the formulated test compound (0.02% active substance) in a spray chamber. Two days after application the plants are inoculated by spraying a sporangia suspension (1.4×10⁵ sporangia/ml) on the test plants. After an incubation period of 4 days at +18° C. and 95% r. h. in a growth chamber the disease incidence is assessed.

Example B-4 Effect Against Plasmopara viticola on Grapevine (Grape Downy Mildew)

5 week old grape seedlings cv. Gutedel are treated with the formulated test compound (0.02% active substance) in a spray chamber. One day after application grape plants are inoculated by spraying a sporangia suspension (4×10⁴ sporangia/ml) on the lower leaf side of the test plants. After an incubation period of 6 days at +22° C. and 95% r. h. in a greenhouse the disease incidence is assessed.

At the indicated concentration compounds 1.01/028;3.01/028; 1.04/028 exhibited over 70% control of the fungal infection in this test.

Example B-5 Residual Protective Activity Against Venturia inaegualis on Apples (Scab on Apple)

4 week old apple seedlings cv. McIntosh are treated with the formulated test compound (0.02% active substance) in a spray chamber. One day after application apple plants are inoculated by spraying a spore suspension (4×10⁵ conidia/ml) on the test plants. After an incubation period of 4 days at +20° C. and 95% r. h. the plants are transferred to standard greenhouse conditions at 20 and 60% r.h. where they stayed for 2 days. After another 4 day incubation period at +20° C. and 95% r. h. the disease incidence is assessed. At the indicated concentration compounds 2.03/028; 1.001/028 exhibited over 70% control of the fungal infection in this test.

Example B-6 Effect Against Erysiphe graminis on Barley (Powdery Mildew on Barley)

a) Residual Protective Activity

Barley plants, cv. Regina of approximately 8 cm height were treated with the formulated test compound (0.02% active substance) in a spray chamber and duste 2 days after inoculation with conidia of the fungus. The infected plants are placed in a greenhouse at +20° C. 6 days after infection, the fungal attack was evaluated.

At the indicated concentration compounds 1.01/028; 1.03/028; 1.04/028, 2.05/028; 2.09/028; 3.014/028; 3.030/028 exhibited over 70% control of the fungal infection in this test.

Example B-7 Botrytis cinerea/Grape (Botrytis on Grapes)

5 week old grape seedlings cv. Gutedel are treated with the formulated test compound (0.02% active substance) in a spray chamber. Two days after application grape plants are inoculated by spraying a spore suspension (1.5×10⁵ conidia/ml) on the test plants. After an incubation period of 3 days at +21° C. and 95% r. h. in a greenhouse the disease incidence is assessed.

At the indicated concentration compounds 1.01/028; 1.03/028; 1.04/028, 1.05/028; 1.06/028, 1.07/028;2.03/028; 2.05/028; 2.08/048; 2.09/028; 3.012/028; 3.013/028;3.014/028; 2.012/028 exhibited over 70% control of the fungal infection in this test.

Example B-8 Effect Against Botrytis cinerea/Tomato (Botrytis on Tomatoes)

4 week old tomato plants cv. Roter Gnom are treated with the formulated test compound 0.02% active substance) in a spray chamber. Two days after application tomato plants are inoculated by spraying a spore suspension (1×10⁵ conidia/ml) on the test plants. After an incubation period of 4 days at +20° C. and 95% r. h. in a greenhouse the disease incidence is assessed.

At the indicated concentration compounds 1.01/028; 2.02/028; 3.01/028; 1.04/028; 1.06/028; 2.06/028; 2.05/028; 2.08/048; 4.02/028; 7.270/028 exhibited over 70% control of the fungal infection in this test.

Example B-9 Effect Against Pyricularia oryzae/Rice (Rice Blast)

3 week old rice plants cv. Sasanishiki are treated with the formulated test compound (0.02% active substance) in a spray chamber. Two days after application rice plants are inoculated by spraying a spore suspension (1×10⁵ conidia/ml) on the test plants. After an incubation period of 6 days at +25° C. and 95% r. h. the disease incidence is assessed. At the indicated concentration compounds 1.02/028; 1.04/028; 2.03/028; 2.06/028; 2.07/028 exhibited over 70% control of the fungal infection in this test.

Example B-10 Effect Against Pyrenophora teres (Helminthosorium)/Barley (Net Blotch on Barley)

1 week old barley plants cv. Regina are treated with a formulated test compound (0.02% active substance) in a spray chamber. Two days. after application barley plants are inoculated by spraying a spore suspension (3×10⁴ conidia/ml) on the test plants. After an incubation period of 2 days at +20° C. and 95% r.h. the disease incidence is assessed. At the indicated concentration compounds 1.01/028; 2.02/028; 3.01/028; 5.01/028; 1.03/028; 1.04/028, 1.01/048; 1.06/028, 1.07/028; 1.08/028; 2.03/028; 2.05/028; 2.07/028; 2.08/048; 2.09/028; 3.012/028; 3.013/028; 3.014/028; 2.012/028; 2.011/028; 3.016/028; 3.017/0283.027/028; 3.028/028; 7.270/028 exhibited over 70% control of the fungal infection in this test.

Example B-11 Effect Against Fusarium culmorum/Wheat (Fusarium Head Blight on Wheat)

A conidia suspension of F. culmorum (7×10⁵ conidia/ml) is mixed with the formulated test compound (0.002% active substance). The mixture is applied into a pouch which has been equipped before with a filter paper. After the application wheat seeds (cv. Orestis) are sown into the upper fault of the filter paper. The prepared pouches are then incubated for 11 days at approx. +10° C. to +18° C. and a relative humidity of 100% with a light period of 14 hours. The evaluation is made by assessing the degree of disease occurrence in the form of brown lesions on the roots.

Example B-12 Effect Against Septoria nodorum/Wheat (Septoria Leaf Spot on Wheat)

1 week old wheat plants cv. Arina are treated with a formulated test compound (0.02% active substance) in a spray chamber. One day after application wheat plants are inoculated by spraying a spore suspension (6×10⁵ conidia/ml) on the test plants. After an incubation period of 1 day at +22° C. and 95% r.h. plants are kept for 7 days at +22° C. and 60% r.h. in a greenhouse. The disease incidence is assessed 8 days after inoculation. At the indicated concentration compounds 1.01/028; 2.02/028; 3.01/028; 5.01/028; 1.03/028; 1.06/028, 1.07/028; 2.03/028; 2.04/028; 2.05/028; 2.06/028; 2.09/028; 3.012/028; 2.012/028; 3.028/028 exhibited over 70% control of the fungal infection in this test. 

1. A compound of formula I

wherein m is 0, 1, 2 or 3; n and p are independently of each other 0 or 1; R₁ is halogen, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted alkenyloxy, optionally substituted alkynyloxy, optionally substituted thioalkyl optionally substituted aryl, COOR₁₁, CONR₁₂R₁₃, S(O)_(q)R₁₄, SO₂NR₁₅R₁₆ or NR_(15a)R_(16a); when there is more than on R₁ group, they may be the same or different; q is 1 or 2; R₂, R_(2a), R₃, R₄, R₅, R₆, R₇, R₈ are each independently hydrogen, optionally substituted alkyl, COR₁₇, COOR₁₈ or optionally substituted aryl, and in addition R₂ and R₃ may also independently be optionally substituted alkoxy, optionally substituted alkenyloxy, optionally substituted alkynyloxy, or optionally substituted alkylthio, COOR₁₉, CONR₂₀R₂₁, OH or SH; R₆ and R₇ may also be independently halogen, optionally substituted alkoxy, optionally substituted alkenyloxy, optionally substituted alkynyloxy, optionally substituted alkenylamino, optionally substituted alkynylamino, optionally substituted alkylthio, optionally substituted cycloalkyl, optionally substituted heteroaryl, optionally substituted hetrocyclyl, optionally substituted cycloalkyloxy, OH, SH, N₃, NR₂₂R₂₃ or N(R₂₄)COR₂₅; or the ring members CR₃R₄ or CR₂R_(2A) are independently of each other a carbonyl group (C═O) or a thonyl group (C═S); or one or two of the adjacent pairs of groups R₉ and R₄, R₄ and R₈, R₅ and R₈, or, if p is zero, R_(2A) and R₈ may form a bond, provided that if there are 2 double bonds in the ring the double bonds are not adjacent each other; or the pair of groups R₇ and R₈ or the pair of groups R₆ and R₇ together with the atom to which they are attached form a C₃-C₇ saturated ring; R₉ is hydrogen, optionally substituted alkyl, optionally substituted alkenyl or optionally substituted alkynyl; R₁₀ is hydrogen, C₁-C₄-alkyl, C₃-C₄-alkenyl, C₃-C₄-alkynyl, —CH₂OR₂₆, CH₂SR₂₇, —C(O)R₂₈, —C(O)OR₂₉, SO₂R₃₀, SOR₃₁ or SR₃₂; R₂₆, R₂₇, R₂₈, R₂₉, R₃₀, R₃₁, R₃₂ are independently C₁-C₈-alkyl C₁-C₈-alkoxyalkyl, CL-CB haloalkyl or phenylC₁-C₂-alkyl wherein the phenyl may be substituted by up to three groups selected from halo or C₁-C₄-alkyl, R₁₁, R₁₂, R₁₃, R₁₄, R₁₅, R₁₆R_(15a), R_(16a), R₁₇, R₁₈, R₁₉, R₂₀, R₂₁, R₂₂, R₂₃, R₂₄, and R₂₅ are independently H or optionally substituted alkyl; or a salt thereof.
 2. A compound according to claim 1, wherein the moiety

is a 5- and 6-membered ring selected from 2,4-dihydro-pyrazol-3-ones, 2,4-dihydro-pyrazole-3-thione, 1H-pyrazoles, 2H-pyridazin-3-ones, 4,5-dihydro-2H-pyridazin-3-ones, 1,2-dihydro-pyrazol-3-ones, 1,2-dihydro-pyrazole-3-thione, pyrazolidin-3-one, pyrazolidine-3-thione, 2H-pyridazin-3-thione and 4,5-dihydro-2H-pyridazin-3-thione.
 3. A compound according to claim 1, wherein R₁ is halogen, C₁₋₃haloalkoxy, CH(OH)R, COR, SO₂NRR′, CH(NR′R″)R, COORa or CONRbRc where Ra, Rb, Rc, R, R′, R″ are independently H or lower alkyl.
 4. A compound according to claim 1, wherein R₂, R_(2A), R₃, R₄, R₅, R₆, R₇, R₈ and R₉ independently of each other are hydrogen or methyl.
 5. A compound according to claim 1, wherein n is zero.
 6. A compound according to claim 1, wherein m is 1 and the R₁ group is at the 3- or 4-position of the phenyl ring.
 7. A compound according to claim 1, wherein R₇ is hydrogen, methyl, ethyl, allyl, propargyl, methoxymethyl, thiomethoxymethyl or ethoxymethyl, more preferably hydrogen or methoxymethyl.
 8. A compound according to claim 1, where R₁₀ is hydrogen, methyl, ethyl, allyl, propargyl, methoxymethyl, thiomethoxymethyl or ethoxymethyl, preferably hydrogen or methoxymethyl.
 9. A compound according to claim 1, wherein the compound is selected from (3-Chloro-phenyl)-{4-[2-(3,4,5-trimethyl-pyrazol-1-yl)-pyridin-4-yl]-pyrimidin-2-yl}-amine; (3-Chloro-phenyl)-{4-[2-(5-methoxy-3-methoxymethyl-pyrazol-1-yl)-pyridin-4-yl]-pyrimidin-2-yl}-amine; (3-Chloro-phenyl)-{4-[2-(5-methoxy-3-methoxymethyl-4-methyl-pyrazol-1-yl)-pyridin-4-yl]-pyrimidin-2-yl}-amine; (3-Chloro-phenyl)-{4-[2-(5-methoxy-4-methyl-pyrazol-1-yl)-pyridin-4-yl]-pyrimidin-2-yl}-amine; (3-Chloro-phenyl)-{4-[2-(5-ethoxy-3,4-dimethyl-pyrazol-1-yl)-pyridin-4-yl]-pyrimidin-2-yl}-amine; 2-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-5-methoxymethyl-1,4-dimethyl-1,2-dihydro-pyrazol-3-one; 2-(4-{2-[(3-Chloro-phenyl)-methoxymethyl-amino]-pyrimidin-4-yl}-pyridin-2-yl)-1,5-dimethyl-1,2-dihydro-pyrazol-3-one; 2-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-1-ethyl-4,5-dimethyl-1,2-dihydropyrazol-3-one; 2-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-1,4-dimethyl-1,2-dihydro-pyrazol-3-one; 2-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-1,5-dimethyl-1,2-dihydro-pyrazol-3-one; 2-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-5-methoxymethyl-4,4-dimethyl-2,4-dihydro-pyrazol-3-one; 2-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-4,4-dimethyl-2,4-dihydro-pyrazol-3-one; 2-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl-4,4,5-trimethyl-2,4-dihydro-pyrazole-3-thione; 5-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-7-methyl-5,6-diaza-spiro[2.4]hept-6-en-4-one; 2-4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-4-ethyl-4,5-dimethyl-2,4-dihydropyrazol-3-one; (3-Chloro-phenyl)-{4-[2-(5-methoxy-3-methyl-pyrazol-1-yl)-pyridin-4-yl]-pyrimidin-2-yl}-amine; 2-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-1,4,5-trimethyl-1,2-dihydro-pyrazol-3-one; 2-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-4,4,5-trimethyl-2,4-dihydro-pyrazol-3-one; 2-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-1,5-dimethyl-1,2-dihydro-pyrazol-3-one; 4,5-Dichloro-2-{4-[2-(3-chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-2H-pyridazin-3-one; 2-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-6-methyl-2H-pyridazin-3-one; 2-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-6-methyl-4,5-dihydro-2H-pyridazin-3-one; 2-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-6-Phenyl-4,5-dihydro-2H-pyridazin-3-one; 4-Chloro-2-{4-[2-(3-chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-5-ethoxy-2H-pyridazin-3-one; 4-Chloro-2-{4-[2-(3-chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-5-ethylsulfanyl-2H-pyridazin-3-one; 5-Azido-4-chloro-2-{4-[2-(3-chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-2H-pyridazin-3-one; 1-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-2-methyl-pyrazolidin-3-one; (3-Chloro-phenyl)-{4-[2-(5-methoxy-3,4-dimethyl-pyrazol-1-yl)-pyridin-4-yl]-pyrimidin-2-yl}-amine; 2-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-5-methoxymethyl-1-methyl-1,2-dihydropyrazol-3-one; 2-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-1,5-dimethyl-3-oxo-2,3-dihydro-1H-pyrazole-4-carbaldehyde; 5-Chloro-2-{4-[2-(3-chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-4-(oxetan-3-yloxy)-2H-pyridazin-3-one; and 4-Chloro-2-{4-[2-(3-chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-5-(tetrahydro-furan-2-ylmethoxy)-2H-pyridazin-3-one.
 10. A composition for controlling and protecting against phytopathogenic microorganisms, comprising a compound of formula I according to claim 1 as active ingredient together with a suitable carrier.
 11. (Cancelled)
 12. A method of controlling and preventing an infestation of crop plants by phytopathogenic microorganisms, which comprises the application of a compound of formula I according to claim 1 as active ingredient to the plant, to parts of plants or to the locus thereof.
 13. A method according to claim 12, wherein the phytopathogenic microorganisms are fungal organisms. 